5-substituted-2,4-diphenylpyrimidine derivatives

ABSTRACT

A compound is disclosed having the formula: ##STR1## wherein R 1  represents a halo-(C 1  to C 6 )-alkoxy group at the ortho or meta position, R 2  and R 3 , which may be either the same or different, each represents a hydrogen atom, a halogen atom, a (C 1  to C 2 )-alkyl group, a halo-(C 1  to C 2 )-alkyl group, a (C 1  to C 2 )-alkoxy group, a nitro group, a (C 1  to C 2 )-alkylthio group, a halo-(C 1  to C 2 )-alkylthio group or a halo-((C 1  to C 2 )-alkoxy group, provided that both of R 2  and R 3 , if each representing a substituent other than a hydrogen atom, are not at the ortho position for the pyrimidine ring at the same time, and W 1  represents a methanesulfonyl group, or a methylthio group; provided that when W 1  is a methylthio group, R 1 , R 2  and R 3  are R 11 , R 22  and R 33  wherein R 11  represents a halo-(C 1  to C 6 )-alkoxy group at the ortho or meta position, R 22  and R 33 , which may be either the same or different, each represents a hydrogen atom, a halogen atom, a (C 1  to C 2 )-alkyl group, a halo-(C 1  to C 2 )-alkyl group, a (C 1  to C 2 )-alkoxy group, or a halo-(C 1  to C 2 )-alkoxy group, and both of R 22  and R 33 , if each representing a substituent other than a hydrogen atom, are not at the ortho position for the pyrimidine ring at the same time.

This is a Divisional application of application Ser. No. 07/809,649filed Dec. 17, 1991, now U.S. Pat. No. 5,190,575 which is a Continuationof application Ser. No. 07/602,833 filed Oct. 23, 1990, which is aContinuation-In-Part of (1) Application Ser. No. 07/544,089 filed Jun.22, 1990, which is a Continuation of application Ser. No. 07/508,446filed Apr. 13, 1990, which is a Divisional of application Ser. No.07/391,016 filed Aug. 9, 1989, now abandoned.

The present invention relates to 5-substituted-2,4-diphenylpyrimidinederivatives, their production and use, and to novel intermediates usefulfor producing such derivatives and their production and use. Moreparticularly, it relates to novel 5-substituted-2,4-diphenylpyrimidinederivatives, a process for producing them, their use as herbicides,intermediates useful for producing them and a process for producing suchintermediates.

There have been used a number of herbicides. However, since they areinsufficient for herbicidal effects, and also poor in the selectivitybetween crops and weeds, they do not always satisfy.

The present inventors have made extensive and intensive studies todevelop excellent herbicides, and consequently found that the followingcompound is good in the herbicidal activity as well as in theselectivity between crops and weeds. The present invention is based onthis finding.

Namely, the compound of the present invention has the followingstructural formula (I); ##STR2## wherein R¹ represents a hydrogen atom,or a halogen atom, a (C₁ to C₃)-alkyl group, a halo-(C₁ to C₃)-alkylgroup, a (C₁ to C₆)-alkoxy group, a (C₂ to C₆)-alkynyloxy group, a (C₂to C₆)-alkenyloxy group, a halo-(C₂ to C₆)-alkynyloxy group, a halo-(C₂to C₆)-alkenyloxy group, a (C₁ to C₂)-alkylthio group, a halo-(C₁ toC₆)-alkoxy group, a halo-(C₁ to C₂)-alkylthio group, a phenoxy group, a(C₁ to C₃)-alkylcarboxy group, a halo-(C₁ to C₃)-alkylcarboxy group, a(C₁ to C₂)-alkoxy-(C₁ to C₂)-alkoxy group, a halo (C₁ toC₂)-alkoxy-halo-(C₂ to C₃)-alkoxy group, a (C₁ to C₃)-alkylsulfonyloxygroup, a halo-(C₁ to C₃)-alkylsulfonyloxy group, a cyano group, a (C₁ toC₃)-alkoxycarbonyl group or an aminomethyl group, at the ortho or metaposition; R² and R³, which may be either the same or different, eachrepresents a hydrogen atom, a halogen atom, a (C₁ to C₂)-alkyl group, ahalo-(C₁ to C₂)-alkyl group, a (C₁ to C₂)-alkoxy group, a nitro group, a(C₁ to C₂)-alkylthio group, a halo-(C₁ to C₂)-alkylthio group or ahalo-(C₁ to C₂)-alkoxy group; and R⁴ represents a (C₁ to C₂)-alkylgroup, provided that R¹, R² and R³ are not a hydrogen atom at the sametime and that both of R² and R³, if each representing a substituentother than a hydrogen atom, are not at the ortho position for thepyrimidine ring at the same time.

Hitherto, J. Heterocyclic Chem., 23, 77 (1986) discloses2,4-diphenyl-5-methanesulfonylpyrimidine, etc. similar to the compoundof the present invention. However, in this paper, no mention is made ofthe biological activity of the compounds. Further, the paper does notdisclose at all the chemical structure and biological activity of5-substituted-2,4-diphenylpyrimidine derivatives of the presentinvention.

The compound of the present invention has an excellent herbicidalactivity, and is good in the selectivity between crops and weeds.Namely, the compound of the present invention has a good herbicidalactivity on a number of undesired weeds, which will cause a problem, bythe foliar treatment as well as the soil treatment in up land fields.Examples of these weeds include broad-leaved weeds such as commonchickweed (Stellaria media), radish (Raphanus sativus), wild mustard(Sinapis arvensis), velvetleaf (Abutilon theophrasti), prickly sida(Sida spinosa), field pansy (Viola arvensis), redroot pigweed(Amaranthus retroflexus), catchweed bedstraw (Galium aparine), ivyleafmorningglory (Ipomoea hederacea), tall morningglory (Pharbitispurpurea), black nightshade (Solanum nigrum), and persian speedwell(Veronica persica); graminaceous weeds such as Japanese millet(Echinochloa frumentacea), annual bluegrass (Poa annua), barnyardgrass(Echinochloa crus-qalli), green foxtail (Setaria viridis), largecrabgrass (Digitaria sanquinalis), oats (Avena sativa), blackgrass(Alopecurus myosuroides), and wild oats (Avena fatua); and Cyperaceousweeds such as hardstem bulrush (Scirpus juncoides) and water nutgrass(Cyperus serotinus). In addition, the compound of the present inventiondoes not exert undesired phytotoxicity to main crops such as wheat,barley, rice plant, soybean, cotton, and corn.

Further, the compound of the present invention has a herbicidal activityon a variety of weeds in paddy fields, for example, graminaceous weedssuch as barnyardgrass (Echinochloa oryzoides), and does not exertundesired phytotoxicity on rice plant.

In the compound of the present invention, it is preferable that R³ is ahydrogen atom. It is also preferable that R¹ is a hydrogen atom, or ahalogen atom, a (C₁ to C₃)-alkyl group, a halo-(C₁ to C₃)-alkyl group, a(C₁ to C₆)-alkoxy group, a (C₂ to C₆)-alkynyloxy group, a (C₂ toC₆)-alkenyloxy group, a halo-(C₂ to C₆)-alkynyloxy group, a halo-(C₂ toC₆)-alkenyloxy group, a (C₁ to C₂)-alkylthio group, a halo-(C₁ toC₆)-alkoxy group, a halo-(C₁ to C₂)-alkylthio group, a phenoxy group, a(C₁ to C₃)-alkylcarboxy group, a halo-(C₁ to C₃)-alkylcarboxy group, a(C₁ to C₂)-alkoxy-(C₁ to C₂)-alkoxy group, a halo-(C₁ toC₂)-alkoxy-halo-(C₂ to C₃)-alkoxy group, a (C₁ to C₃)-alkylsulfonyloxygroup, a halo-(C₁ to C₃)-alkylsulfonyloxy group or a cyano group, at themeta position; and R² and R³, which may be either the same or different,each is a hydrogen atom, or a halogen atom, a (C₁ to C₂)-alkyl group, ahalo-(C₁ to C₂)-alkyl group or a (C₁ to C₂)-alkoxy group, at the meta orpara position. Among the above compounds, preferred are those that R¹and R² are as described above and R³ is a hydrogen atom.

More preferably, R¹ is a hydrogen atom, or a halogen atom, atrifluoromethyl group or a trihalomethoxy group, at the meta position;R² and R³, which may be either the same or diferrent, each is a hydrogenatom, or a halogen atom or a trifluoromethyl group, at the meta or paraposition; and R⁴ is a methyl group. Among the above compounds, preferredare those that R¹ is as described above, R² is a hydrogen atom, or ahalogen atom or a trifluoromethyl group, at the para position, and R³ isa hydrogen atom. Further more preferably, R¹ is a trifluoromethyl groupor a trifluoromethoxy group, at the meta position; R² and R³, which maybe either the same or different, each is a fluorine atom, a chlorineatom or a trifluoromethyl group, at the meta or para position; and R⁴ isa methyl group. Most preferably, R¹ is a trifluoromethyl group or atrifluoromethoxy group, at the meta position; R² is a fluorine atom, achlorine atom or a trifluoromethyl group, at the para position; R³ is ahydrogen atom; and R⁴ is a methyl group.

It is also preferable that R² and R³, which may be either the same ordifferent, each is a halogen atom or a halo-(C₁ to C₂)-alkyl group, morepreferably, each is a halogen atom or a trifluoromethyl group at themeta or para position.

The particularly preferred compounds of the present invention include2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine;2-(4-trifluoromethylphenyl)-4-(3-trifluoromethoxyphenyl)-5-methoxypyrimidine;and 2-(4-fluorophenyl)-4-(3-trifluoromethoxyphenyl)-5-methoxypyrimidine.

The compound (I) of the present invention can be produced through thefollowing reaction scheme: ##STR3##

Procedure (A):

The compound (I) is prepared by reacting a compound of the formula(II-1): ##STR4## [wherein R¹, R² and R³ are each as defined above] witha compound of the formula (III):

    R.sup.4 OM                                                 (III)

[wherein M is a metal atom (e.g., sodium), and R⁴ is as defined above].

The reaction is usually carried out in an inert solvent at a temperatureof about 20° to 100° C. for a period of about 0.5 to 5 hours.

Normally, the compound (III) is used in an amount of about 1 to 10equivalents to one equivalent of the compound (II-1).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), alcohols(e.g., methanol, ethanol, isopropanol, t-butanol), esters (e.g., ethylacetate, butyl acetate), acid amides (e.g., N,N-dimethylformamide,acetamide), sulfur compounds (e.g., dimethyl sulfoxide), and mixturesthereof.

The compound (III) includes alkali metal alkoxides (e.g., sodiummethoxide, sodium ethoxide).

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., to obtain the compound (I) of the presentinvention, and if necessary, purified by chromatography, distillation,recrystallization, etc.

Procedure (B)

A compound of the formula (I-1): ##STR5## [wherein R⁵ is a (C₂ toC₆)-alkoxy group, a halo-(C₁ to C₂)-alkoxy-halo-(C₂ to C₃)-alkoxy groupor a halo-(C₂ to C₆)-alkoxy group, at the ortho or meta position; andR², R³ and R⁴ are each as defined above] is prepared by reacting acompound of the formula (IV): ##STR6## [wherein R², R³ and R⁴ are eachas defined above; and the hydroxyl group of the phenol moiety bonded tothe pyrimidine ring is positioned, at the ortho or meta position] with a(C₂ to C₆)-olefin which may be substituted with halogen or halo-(C₁ toC₂)-alkoxy group.

The reaction is usually carried out in the presence of a base in aninert solvent at a temperature of 30° to 150° C. for a period of about 1to 100 hours.

Normally, the olefin and the base are used respectively in amounts ofabout 5 to 30 equivalents and of about 1 to 10 equivalents to oneequivalent of the compound (IV).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chlorobenzene,dichlorobenzene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), nitriles(e.g., acetonitrile, isobutyronitrile), acid amides (e.g.,N,N-dimethylformamide, acetamide), water, and mixtures thereof.

The base includes inorganic bases (e.g., sodium hydroxide, potassiumhydroxide, sodium carbonate, potassium carbonate, sodium hydride), etc.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,distillation, recrystallization, etc.

Procedure (C)

A compound of the formula (I-2): ##STR7## [wherein R⁶ is a (C₁ toC₃)-alkylsulfonyloxy group or a halo-(C₁ to C₃)-alkylsulfonyloxy group,at the ortho or meta position; and R², R³ and R⁴ are each as definedabove] is prepared by reacting a compound of the formula (V):

    R.sup.7 --Cl                                               (V)

[wherein R⁷ is a (C₁ to C₃)-alkylsulfonyl group which may be substitutedwith halogen] with the compound (IV).

The reaction is usually carried out with or without an inert solvent andin the presence of a base at a temperature of about 0° to 50° C. for aperiod of about 0.5 to 5 hours.

Normally, the compound (V) and the base are used respectively in amountsof about 1 to 2 equivalents and of about 1 to 5 equivalents to oneequivalent of the compound (IV).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chloroform, carbontetrachloride, dichloroethane, chlorcbenzene, dichlorobenzene), ethers(e.g., diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran,diethylene glycol dimethyl ether), ketones (e.g., acetone, methyl ethylketone, methyl isobutyl ketone, isophorone, cyclohexanone), esters(e.g., ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate),pyridine, acid amides (e.g., N,N-dimethylformamide, acetamide), water,and mixtures thereof.

The base includes organic bases (e.g., pyridine), etc.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,distillation, recrystallization, etc. Procedure (D):

A compound of the formula (I-3): ##STR8## [wherein R⁸ is a (C₁ toC₆)-alkoxy group which may contain an unsaturated bond, at the ortho ormeta position; and R², R³ and R⁴ are each as defined above] is preparedby reacting a compound of the formula (VI):

    R.sup.9 --X                                                (VI)

[wherein R⁹ is a (C₁ to C₆)-alkyl group, a (C₂ to C₆)-alkenyl group or a(C₂ to C₆)-alkynyl group; and X is a halogen atom] with the compound(IV).

The reaction is usually carried out in the presence of a base in aninert solvent at a temperature of 20° to 150° C. for a period of about0.5 to 50 hours.

Normally, the compound (VI) and the base are used respectively inamounts of about 1 to 20 equivalents and of about 1 to 20 equivalents toone equivalent of the compound (IV).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), ketones(e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone,cyclohexanone), esters (e.g., ethyl formate, ethyl acetate, butylacetate, diethyl carbonate), nitriles (e.g., acetonitrile,isobutyronitrile), acid amides (e.g., N,N-dimethylformamide, acetamide),and water.

The base includes inorganic bases (e.g., sodium hydroxide, potassiumhydroxide, sodium carbonate, potassium carbonate, sodium hydride), etc.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc , and if necessary, purified by chromatography,distillation, recrystallization, etc. Procedure (E):

A compound of the formula (I-4): ##STR9## [wherein R¹⁰ is a (C₁ toC₃)-acyl group which may be substituted with a halogen atom; and R², R³and R⁴ are each as defined above] is prepared by reacting a compound ofthe formula (VII):

    R.sup.10 --O--R.sup.10                                     (VII)

[wherein R¹⁰ is as defined above] with the compound (IV).

The reaction is usually carried out with or without an inert solvent andin the presence of an acid catalyst at a temperature of about 0° to 100°C. for a period of about 0.5 to 30 hours.

Normally, the compound (VII) is used in an amount of about 1 to 3equivalents to one equivalent of the compound (IV).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chloroform, carbontetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers(e.g., diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran,diethylene glycol dimethyl ether), ketones (e.g., acetone, methyl ethylketone, methyl isobutyl ketone, isophorone, cyclohexanone), acid amides(e.g, N,N,-dimethylformamide, acetamide), water, and mixtures thereof.

The acid catalyst includes organic acids (e.g., acetic acid), inorganicacids (e.g., hydrochloric acid, sulfuric acid), etc.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,distillation, recrystallization, etc.

Table 1 illustrates examples of the compound (I) of the presentinvention which can be produced by the procedures (A)˜(E).

                  TABLE 1                                                         ______________________________________                                         ##STR10##                                                                    R.sup.1      R.sup.2     R.sup.3  R.sup.4                                     ______________________________________                                        H            4-Cl        H        CH.sub.3                                    H            4-Br        H        CH.sub.3                                    H            4-CF.sub.3  H        CH.sub.3                                    H            4-NO.sub.2  H        CH.sub.3                                    m-F          H           H        CH.sub.3                                    m-F          4-CH.sub.3  H        CH.sub.3                                    m-F          4-F         H        CH.sub.3                                    m-F          4-CF.sub.3  H        CH.sub.3                                    m-F          4-Cl        H        CH.sub.3                                    m-F          4-Br        H        CH.sub.3                                    m-F          4-F         H        C.sub.2 H.sub.5                             m-Cl         4-F         H        CH.sub.3                                    m-Cl         H           H        CH.sub.3                                    m-Cl         4-Cl        H        CH.sub.3                                    m-Cl         4-CF.sub.3  H        CH.sub.3                                    m-Br         H           H        CH.sub.3                                    m-Br         4-Cl        H        CH.sub.3                                    m-Br         4-Br        H        CH.sub.3                                    m-Br         4-CF.sub.3  H        CH.sub.3                                    m-Br         4-NO.sub.2  H        CH.sub.3                                    m-Br         4-F         H        C.sub.2 H.sub. 5                            o-Br         4-CF.sub.3  H        CH.sub.3                                    m-I          4-CF.sub.3  H        CH.sub.3                                    m-I          4-F         H        CH.sub.3                                    m-I          4-F         H        C.sub.2 H.sub.5                             m-CH.sub.3   4-F         H        CH.sub.3                                    m-CH.sub.3   4-CF.sub.3  H        CH.sub.3                                    o-CH.sub.3   4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3   H           H        CH.sub.3                                    m-CF.sub.3   4-CH.sub.3  H        CH.sub.3                                    m-CF.sub.3   4-F         H        CH.sub.3                                    m-CF.sub.3   4-Cl        H        CH.sub.3                                    m-CF.sub.3   4-Br        H        CH.sub.3                                    m-CF.sub.3   4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3   4-CH.sub.3 O                                                                              H        CH.sub.3                                    m-CF.sub.3   3-CH.sub.3 O                                                                              H        CH.sub.3                                    m-CF.sub.3   3-F         H        CH.sub.3                                    m-CF.sub.3   2-F         H        CH.sub.3                                    m-CF.sub.3   4-F         H        C.sub.2 H.sub.5                             m-CF.sub.3   4-CF.sub.3  H        C.sub.2 H.sub.5                             m-CF.sub.3   4-Cl        H        C.sub.2 H.sub.5                             m-CF.sub.3   4-CH.sub.3  H        C.sub.2 H.sub.5                             m-CF.sub.3   H           H        C.sub.2 H.sub.5                             o-CF.sub.3   4-CF.sub.3  H        CH.sub.3                                    o-CF.sub.3   2-F         H        CH.sub.3                                    m-CH.sub.3 O 4-F         H        CH.sub.3                                    m-CH.sub.3 O 4-CF.sub.3  H        CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        4-F         H        CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        4-CF.sub.3  H        CH.sub.3                                    m-(i)C.sub. 3 H.sub.7 O                                                                    4-F         H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   4-F         H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    4-F         H        CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    4-CF.sub.3  H        CH.sub.3                                    m-CHCCH.sub.2 O                                                                            4-F         H        CH.sub.3                                    m-CHCCH.sub.2 O                                                                            4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.3 S 4-F         H        CH.sub.3                                    m-CH.sub.3 S 4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 O 4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 O 4-F         H        CH.sub.3                                    m-CF.sub.3 O 4-Cl        H        CH.sub.3                                    m-CF.sub.3 O 4-F         H        C.sub.2 H.sub.5                             m-CCl.sub.3 O                                                                              4-F         H        CH.sub.3                                    m-CCl.sub.3 O                                                                              4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.2 HO                                                                              4-F         H        CH.sub.3                                    m-CF.sub.2 HO                                                                              4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.2 ClO                                                                             4-F         H        CH.sub.3                                    m-CF.sub.2 ClO                                                                             4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      4-F         H        CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     4-F         H        CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     4-CF.sub.3  H        CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    4-F         H        CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 S 4-F         H        CH.sub.3                                    m-CF.sub.3 S 4-CF.sub.3  H        CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        4-F         H        CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        4-F         H        CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        4-CF.sub.3  H        CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          4-F         H        CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          4-CF.sub.3  H        CH.sub.3                                    m-CClFHCClFO 4-F         H        CH.sub.3                                    m-CClFHCClFO 4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 CO.sub.2                                                                        4-F         H        CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     4-F         H        CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        4-F         H        CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.3 CH.sub.2 SO.sub.3                                                               4-F         H        CH.sub.3                                    m-CH.sub.3 CH.sub.2 SO.sub.3                                                               4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        4-F         H        CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               4-F         H        CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 O 4-CF.sub.3 O                                                                              H        CH.sub.3                                    m-CF.sub.3   4-CF.sub.3 O                                                                              H        CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        4-CF.sub.3  H        CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        4-F         H        CH.sub.3                                    m-CF.sub.3 O 4-SCH.sub.3 H        CH.sub.3                                    m-CF.sub.3   4-SCH.sub.3 H        CH.sub.3                                    m-CN         4-CF.sub.3  H        CH.sub.3                                    m-CN         4-F         H        CH.sub.3                                    m-COOCH.sub.3                                                                              4-CF.sub.3  H        CH.sub.3                                    m-COOCH.sub.3                                                                              4-F         H        CH.sub.3                                    m-CClFCFO    4-F         H        CH.sub.3                                    m-CF.sub.3 O 4-SCF.sub.3 H        CH.sub.3                                    m-CF.sub.3   4-SCF.sub.3 H        CH.sub.3                                    H            4-F         H        CH.sub.3                                    H            3-F         H        CH.sub.3                                    H            3-CF.sub.3  H        CH.sub.3                                    H            4-CH.sub.3  H        CH.sub.3                                    m-F          3-F         H        CH.sub.3                                    m-F          3-CF.sub.3  H        CH.sub.3                                    m-Cl         3-F         H        CH.sub.3                                    m-Cl         3-CF.sub.3  H        CH.sub.3                                    m-Cl         4-CH.sub.3  H        CH.sub.3                                    m-CF.sub.3   3-CF.sub.3  H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     H           H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     4-CF.sub.3  H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     3-F         H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     3-CF.sub.3  H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     4-Cl        H        CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     4-CH.sub.3  H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   H           H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   3-F         H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   3-CF.sub.3  H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   4-Cl        H        CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   4-CH.sub.3  H        CH.sub.3                                    m-CF.sub.3 O H           H        CH.sub.3                                    m-CF.sub.3 O 3-F         H        CH.sub.3                                    m-CF.sub.3 O 3-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 O 4-CH.sub.3  H        CH.sub.3                                    o-CF.sub.3   H           H        CH.sub.3                                    o-CF.sub.3   4-F         H        CH.sub.3                                    o-CF.sub.3   3-F         H        CH.sub.3                                    o-CF.sub.3   3-CF.sub.3  H        CH.sub.3                                    o-CF.sub.3   4-Cl        H        CH.sub.3                                    o-CF.sub.3   4-CH.sub.3  H        CH.sub.3                                    H            2-F         4-Cl     CH.sub.3                                    H            3-F         4-Cl     CH.sub.3                                    H            2-F         4-Br     CH.sub.3                                    H            3-F         4-F      CH.sub.3                                    H            2-F         4-CF.sub.3                                                                             CH.sub.3                                    H            3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-F          2-F         4-F      CH.sub.3                                    m-F          3-F         4-F      CH.sub.3                                    m-F          2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-F          3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-F          2-F         4-Cl     CH.sub.3                                    m-F          3-F         4-Cl     CH.sub.3                                    m-F          2-F         4-Br     CH.sub.3                                    m-F          3-F         4-Br     CH.sub.3                                    m-F          2-F         4-F      C.sub.2 H.sub.5                             m-F          3-F         4-F      C.sub.2 H.sub.5                             m-Cl         2-F         4-F      CH.sub.3                                    m-Cl         3-F         4-F      CH.sub.3                                    m-Cl         2-F         4-Cl     CH.sub.3                                    m-Cl         3-F         4-Cl     CH.sub.3                                    m-Cl         2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-Cl         3-F         4-CF.sub.3                                                                             CH.sub.3                                    o-Br         2-F         4-CF.sub.3                                                                             CH.sub.3                                    o-Br         3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-I          2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-I          3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-I          2-F         4-F      CH.sub.3                                    m-I          3-F         4-F      CH.sub.3                                    m-I          2-F         4-F      C.sub.2 H.sub.5                             m-I          3-F         4-F      C.sub.2 H.sub.5                             m-CH.sub.3   2-F         4-F      CH.sub.3                                    m-CH.sub.3   3-F         4-F      CH.sub.3                                    m-CH.sub.3   2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3   3-F         4-CF.sub.3                                                                             CH.sub.3                                    o-CH.sub.3   2-F         4-CF.sub.3                                                                             CH.sub.3                                    o-CH.sub.3   3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3   3-F         5-F      CH.sub.3                                    m-CF.sub.3   2-F         4-F      CH.sub.3                                    m-CF.sub.3   3-F         4-F      CH.sub.3                                    m-CF.sub.3   2-F         4-Cl     CH.sub.3                                    m-CF.sub.3   3-F         4-Cl     CH.sub.3                                    m-CF.sub.3   2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3   3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3   3-CF.sub.3  4-F      CH.sub.3                                    m-CF.sub.3   3-Cl        4-F      CH.sub.3                                    m-CF.sub.3   2-F         4-CF.sub.3                                                                             C.sub.2 H.sub.5                             m-CF.sub.3   3-F         4-CF.sub.3                                                                             C.sub.2 H.sub.5                             m-CF.sub.3   2-F         4-Cl     C.sub.2 H.sub.5                             m-CF.sub.3   3-F         4-Cl     C.sub.2 H.sub.5                             m-CH.sub.3 O 2-F         4-F      CH.sub.3                                    m-CH.sub.3 O 3-F         4-F      CH.sub.3                                    m-CH.sub.3 O 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 O 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        2-F         4-F      CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        3-F         4-F      CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.2 H.sub.5 O                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     2-F         4-F      CH.sub.3                                    m-(i)C.sub.3 H.sub.7 O                                                                     3-F         4-F      CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   2-F         4-F      CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   3-F         4-F      CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-(sec)C.sub.4 H.sub.9 O                                                                   3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    2-F         4-F      CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    3-F         4-F      CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.2 CHCH.sub.2 O                                                                    3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH CCH.sub.2 O                                                                           2-F         4-F      CH.sub.3                                    m-CHCCH.sub.2 O                                                                            3-F         4-F      CH.sub.3                                    m-CHCCH.sub.2 O                                                                            2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CHCCH.sub.2 O                                                                            3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 S 2-F         4-F      CH.sub.3                                    m-CH.sub.3 S 3-F         4-F      CH.sub.3                                    m-CH.sub.3 S 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 S 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 O 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 O 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 O 3-CF.sub.3  4-F      CH.sub.3                                    m-CF.sub.3 O 2-F         4-F      CH.sub.3                                    m-CF.sub.3 O 3-F         4-F      CH.sub.3                                    m-CF.sub.3 O 2-F         4-Cl     CH.sub.3                                    m-CF.sub.3 O 3-F         4-Cl     CH.sub.3                                    m-CF.sub.3 O 3-Cl        4-F      CH.sub.3                                    m-CF.sub.3 O 2-F         4-F      C.sub.2 H.sub.5                             m-CF.sub.3 O 3-F         4-F      C.sub.2 H.sub.5                             m-CCl.sub.3 O                                                                              2-F         4-F      CH.sub.3                                    m-CCl.sub.3 O                                                                              3-F         4-F      CH.sub.3                                    m-CCl.sub.3 O                                                                              2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CCl.sub.3 O                                                                              3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 HO                                                                              2-F         4-F      CH.sub.3                                    m-CF.sub.2 HO                                                                              3-F         4-F      CH.sub.3                                    m-CF.sub.2 HO                                                                              2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 HO                                                                              3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 ClO                                                                             2-F         4-F      CH.sub.3                                    m-CF.sub.2 ClO                                                                             3-F         4-F      CH.sub.3                                    m-CF.sub.2 ClO                                                                             2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 ClO                                                                             3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      2-F         4-F      CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      3-F         4-F      CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 CF.sub.2 O                                                                      3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     2-F         4-F      CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     3-F         4-F      CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 HCF.sub.2 O                                                                     3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    2-F         4-F      CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    3-F         4-F      CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CCl.sub.2 HCF.sub.2 O                                                                    3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 BrO                                                                             2-F         4-F      CH.sub.3                                    m-CF.sub.2 BrO                                                                             3-F         4-F      CH.sub.3                                    m-CF.sub.2 BrO                                                                             2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 BrO                                                                             3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 S 2-F         4-F      CH.sub.3                                    m-CF.sub.3 S 3-F         4-F      CH.sub.3                                    m-CF.sub.3 S 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 S 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        2-F         4-F      CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        3-F         4-F      CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.6 H.sub.5 O                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        2-F         4-F      CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        3-F         4-F      CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 CO.sub.2                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          2-F         4-F      CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          3-F         4-F      CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CClFHCF.sub.2 O                                                                          3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CClFHCClFO 2-F         4-F      CH.sub.3                                    m-CClFHCClFO 3-F         4-F      CH.sub.3                                    m-CClFHCClFO 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CClFHCClFO 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 CO.sub.2                                                                        2-F         4-F      CH.sub.3                                    m-CF.sub.3 CO.sub.2                                                                        3-F         4-F      CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     2-F         4-F      CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     3-F         4-F      CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 OCH.sub.2 O                                                                     3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        2-F         4-F      CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        3-F         4-F      CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.3 SO.sub.3                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.2 H.sub.5 SO.sub.3                                                                 2-F         4-F      CH.sub.3                                    m-C.sub.2 H.sub.5 SO.sub.3                                                                 3-F         4-F      CH.sub.3                                    m-C.sub.2 H.sub.5 SO.sub.3                                                                 2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-C.sub.2 H.sub.5 SO.sub.3                                                                 3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        2-F         4-F      CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        3-F         4-F      CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 SO.sub.3                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               2-F         4-F      CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               3-F         4-F      CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.3 CF.sub.2 SO.sub.3                                                               3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        2-F         4-F      CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        3-F         4-F      CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CH.sub.2 NH.sub.2                                                                        3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CN         2-F         4-F      CH.sub.3                                    m-CN         3-F         4-F      CH.sub.3                                    m-CN         2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CN         3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-COOCH.sub.3                                                                              2-F         4-F      CH.sub.3                                    m-COOCH.sub.3                                                                              3-F         4-F      CH.sub.3                                    m-COOCH.sub.3                                                                              2-F         4-CF.sub.3                                                                             CH.sub.3                                    m-COOCH.sub.3                                                                              3-F         4-CF.sub.3                                                                             CH.sub.3                                    m-CF.sub.2 BrO                                                                             4-F         H        CH.sub.3                                    m-CF.sub.2 BrO                                                                             4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.2 BrCF.sub.2 O                                                                    4-F         H        CH.sub.3                                    m-CF.sub.2 BrCF.sub.2 O                                                                    4-CF.sub.3  H        CH.sub.3                                    m-CF.sub.3 OCFHCF.sub.2 O                                                                  4-F         H        CH.sub.3                                    m-CF.sub.3 OCFHCF.sub.2 O                                                                  4-CF.sub.3  H        CH.sub.3                                    ______________________________________                                    

The present invention will be illustrated in more detail by thefollowing examples, but the present invention is not construed as beinglimited thereto.

First, Production Examples of the present invention are shown below.

PRODUCTION EXAMPLE 1

2 g of2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine,0.3 g of sodium methoxide and 20 ml of methanol were added to 120 ml ofethylene glycol dimethyl ether, and the resulting mixture was heatedunder reflux for 5 hours. The solvent was distilled away under reducedpressure. The residue was washed with water, and then dried to obtain1.5 g of2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine(Compound 18).

PRODUCTION EXAMPLE 2

1.5 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine and0.25 g of sodium hydride were added to 15 ml of N,N-dimethylformamide,and the resulting mixture was heated to 70° C. After adding 6.6 g of1,1-dichloro-2,2-difluoroethylene thereto, the mixture was heated underreflux for 3 days. After completion of the reaction, ice-cold water wasadded to the mixture. Subsequently the mixture was extracted with ethylacetate. The solvent was evaporated off, and the residue was purified bycolumn chromatography on silica gel, thereby obtaining 1.0 g of2-(4-fluorophenyl)-4-[3-(1',1'-difluoro-2',2'-dichloroethoxy)phenyl]-5-methoxypyrimidine (Compound 53).

PRODUCTION EXAMPLE 3

1.2 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine and0.57 g of methanesulfonyl chloride were added to 10 ml of pyridine, andthe resulting mixture was stirred for 3 hours at room temperature. Aftercompletion of the reaction, ice-cold water was added to the mixture.Subsequently, the mixture was extracted with ethyl acetate. The solventwas evaporated off, and the residue was purified by columnchromatography on silica gel, thereby obtaining 1.0 g2-(4-fluorophenyl)-4-(3-methanesulfonyloxyphenyl)-5-methoxypyrimidine(Compound 54).

PRODUCTION EXAMPLE 4

1.2 g of 2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine, 5.5g of potassium carbonate, and 5.5 g of 2-bromobutane were added to 200ml of acetone, and the resulting mixture was heated under reflux for 2days. The solvent was distilled away under reduced pressure. The residuewas washed with water, and then purified by column chromatography onsilica gel, thereby obtaining 1.0 g of2-(4-fluorophenyl)-4-[3-sec-butoxyphenyl)-5-methoxypyrimidine (Compound50).

PRODUCTION EXAMPLE 5

One drop of 96% sulfuric acid was added to a mixture of 1.2 g of2-(4-fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine and 0.5 g ofacetic anhydride, and the resulting mixture was stirred for 20 hours atroom temperature. After completion of the reaction, ice-cold water wasadded to mixture. Subsequently, the mixture was extracted with ethylacetate. The solvent was evaporated off, and the residue was purified bycolumn chromatography on silica gel thereby obtaining 1.0 g of2-(4-fluorophenyl)-4-(3-acetoxyphenyl)-5-methoxypyrimidine (Compound55).

PRODUCTION EXAMPLE 6

2.1 g of2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine,0.3 g of sodium methoxide and 20 ml of methanol were added to 120 ml ofethylene glycol dimethyl ether and the resulting mixture was heatedunder reflux for 5 hours. The solvent was distilled away under reducedpressure. The residue was washed with water and then dried to obtain1.55 g of2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methoxypyrimidine(Compound 77).

Table 2 illustrates part of the compounds of the present inventionproduced according to the above Production Examples.

                                      TABLE 2                                     __________________________________________________________________________     ##STR11##                                                                    Compound                                                                      No.   R.sup.1    R.sup.2                                                                            R.sup.3                                                                           R.sup.4                                             __________________________________________________________________________                                   Melting Point (°C.)                      1    m-Cl       4-F  H   CH.sub.3                                                                           126.0                                           2    H          4-Cl H   CH.sub.3                                                                           105.5                                           3    H          4-Br H   CH.sub.3                                                                           155.4                                           4    H          4-CF.sub.3                                                                         H   CH.sub.3                                                                           84.4                                            5    H          4-NO.sub.2                                                                         H   CH.sub.3                                                                           163.5                                           6    m-Cl       H    H   CH.sub.3                                                                           97.0                                            7    m-Cl       4-Cl H   CH.sub.3                                                                           143.0                                           8    m-Cl       4-CF.sub.3                                                                         H   CH.sub.3                                                                           97.0                                            9    m-Br       H    H   CH.sub.3                                                                           103.2                                          10    m-Br       4-Cl H   CH.sub.3                                                                           153.3                                          11    m-Br       4-Br H   CH.sub.3                                                                           158.9                                          12    m-Br       4-CF.sub.3                                                                         H   CH.sub.3                                                                           124.5                                          13    m-Br       4-NO.sub.2                                                                         H   CH.sub.3                                                                           152.1                                                                         (dec)                                          14    o-Br       4-CF.sub. 3                                                                        H   CH.sub.3                                                                           119.0                                          15    o-CH.sub.3 4-CF.sub.3                                                                         H   CH.sub.3                                                                           103.4                                          16    m-CF.sub.3 H    H   CH.sub.3                                                                           92.6                                           17    m-CF.sub.3 4-CH.sub.3                                                                         H   CH.sub.3                                                                           95.8                                           18    m-CF.sub.3 4-F  H   CH.sub.3                                                                           98.9                                           19    m-CF.sub.3 4-Cl H   CH.sub.3                                                                           127.4                                          20    m-CF.sub.3 4-Br H   CH.sub.3                                                                           130.5                                          21    m-CF.sub.3 4-CF.sub.3                                                                         H   CH.sub.3                                                                           108.3                                          22    m-CF.sub.3 4-CH.sub.3 O                                                                       H   CH.sub.3                                                                           104.3                                          23    m-I        4-CF.sub.3                                                                         H   CH.sub.3                                                                           131.4                                          24    m-F        H    H   CH.sub.3                                                                           83.5                                           25    m-F        4-CH.sub.3                                                                         H   CH.sub.3                                                                           72.5                                           26    m-F        4-F  H   CH.sub.3                                                                           98.3                                           27    m-F        4-CF.sub.3                                                                         H   CH.sub.3                                                                           101.3                                          28    m-F        4-Cl H   CH.sub.3                                                                           104.5                                          29    m-F        4-Br H   CH.sub.3                                                                           131.2                                          30    o-CF.sub.3 4-CF.sub.3                                                                         H   CH.sub.3                                                                           142.5                                          31    m-CF.sub.3 O                                                                             4-CF.sub.3                                                                         H   CH.sub.3                                                                           94.6                                           32    m-CF.sub.3 O                                                                             4-F  H   CH.sub.3                                                                           73.9                                           33    m-I        4-F  H   CH.sub.3                                                                           111.5                                          34    m-CF.sub.3 4-F  H   C.sub.2 H.sub.5                                                                    90.6                                           35    m-CF.sub.3 4-CF.sub.3                                                                         H   C.sub.2 H.sub.5                                                                    101.4                                          36    m-CF.sub.3 4-Cl H   C.sub.2 H.sub.5                                                                    103.0                                          37    m-CF.sub.3 4-CH.sub.3                                                                         H   C.sub. 2 H.sub.5                                                                   98.4                                           38    m-CF.sub.3 H    H   C.sub.2 H.sub.5                                                                    104.1                                          39    m-Br       4-F  H   C.sub.2 H.sub.5                                                                    110.0                                          40    m-F        4-F  H   C.sub.2 H.sub.5                                                                    111.9                                          41    m-I        4-F  H   C.sub.2 H.sub.5                                                                    122.5                                          42    m-CF.sub.3 O                                                                             4-F  H   C.sub.2 H.sub.5                                                                    66.6                                           43    m-CH.sub.3 4-F  H   CH.sub.3                                                                           106.7                                          44    m-C.sub.2 H.sub.5 O                                                                      4-F  H   CH.sub.3                                                                           86.1                                           45    m-CH.sub.3 OCH.sub.2 O                                                                   4-F  H   CH.sub.3                                                                           93.4                                           46    m-CH.sub.3 O                                                                             4-F  H   CH.sub.3                                                                           90.2                                           47    m-(i)C.sub.3 H.sub.7 O                                                                   4-F  H   CH.sub.3                                                                           78.2                                           48    m-CF.sub.3 O                                                                             4-Cl H   CH.sub.3                                                                           95.3                                           49    m-CF.sub.2 HCF.sub.2 O                                                                   4-F  H   CH.sub.3                                                                           79.2                                           50    m-(sec)C.sub.4 H.sub.9 O                                                                 4-F  H   CH.sub.3                                                                           86.0                                           51    m-C.sub.6 H.sub.5 O                                                                      4-F  H   CH.sub.3                                                                           150.4                                          52    m-CF.sub.3 2-F  H   CH.sub.3                                                                           67.8                                           53    m-CCl.sub.2 HCF.sub.2 O                                                                  4-F  H   CH.sub.3                                                                           75.5                                           54    m-CH.sub.3 SO.sub.3                                                                      4-F  H   CH.sub.3                                                                           121.4                                          55    m-CH.sub.3 CO.sub.2                                                                      4-F  H   CH.sub.3                                                                           113.6                                          56    m-CF.sub.3 CO.sub.2                                                                      4-F  H   CH.sub.3                                                                           147.4                                          57    m-CF.sub.3 3-CH.sub.3 O                                                                       H   CH.sub.3                                                                           83.1                                           58    m-CF.sub.3 3-F  H   CH.sub.3                                                                           60.0                                           59    m-CF.sub.3 SO.sub.3                                                                      4-F  H   CH.sub.3                                                                           127.5                                          60    m-CH.sub.3 O                                                                             4-CF.sub.3                                                                         H   CH.sub.3                                                                           98.2                                           61    m-C.sub.2 H.sub.5 O                                                                      4-CF.sub.3                                                                         H   CH.sub.3                                                                           86.4                                           62    m-CH.sub.3 OCH.sub.2 O                                                                   4-CF.sub.3                                                                         H   CH.sub.3                                                                           79.3                                           63    m-C.sub.6 H.sub.5 O                                                                      4-CF.sub.3                                                                         H   CH.sub.3                                                                           132.2                                          64    m-CF.sub.3 3-CF.sub.3                                                                         H   CH.sub.3                                                                           98.2                                           65    m-CF.sub.3 O                                                                             3-F  H   CH.sub.3                                                                           51.6                                           66    m-CF.sub.3 O                                                                             3-CF.sub.3                                                                         H   CH.sub.3                                                                           55.7                                           67    m-CH.sub.2 CHCH.sub.2 O                                                                  4-F  H   CH.sub.3                                                                           1.6180                                                                        (n.sub.D.sup.25)                               68    m-CF.sub.3 3-Cl H   CH.sub.3                                                                           78.8                                           69    m-CF.sub.2 HO                                                                            4-CF.sub.3                                                                         H   CH.sub.3                                                                           93.4                                           70    m-CF.sub.3 O                                                                             3-Cl H   CH.sub.3                                                                           77.8                                           71    m-CF.sub.3 4-SCH.sub.3                                                                        H   CH.sub.3                                                                           121.1                                          72    m-CN       4-CF.sub.3                                                                         H   CH.sub.3                                                                           131.7                                          73    m-CF.sub.2 HO                                                                            4-F  H   CH.sub.3                                                                           88.5                                                                          .sup.1 H-NMR (δ value)*                  74    m-CF.sub.3 O                                                                             2-F  4-F CH.sub.3                                                                           8.40  (s, 1H),                                                                8.35˜6.65                                                                    (m, 7H),                                                                 3.95 (s, 3H)                                   75    m-CF.sub.3 O                                                                             3-F  4-F CH.sub.3                                                                           8.45˜6.90                                                                    (m, 8H),                                                                 4.0  (s, 3H)                                   76    m-CF.sub.3 O                                                                             3-F  5-F CH.sub.3                                                                           8.35 (s, 1H),                                                                 8.20˜6.50                                                                    (m, 7H),                                                                 3.95 (s, 3H)                                   77    m-CF.sub.3 2-F  4-F CH.sub.3                                                                           8.55˜6.70                                                                    (m, 8H),                                                                 4.05 (s, 3H)                                   78    m-CF.sub.3 3-F  4-F CH.sub.3                                                                           8.40˜6.90                                                                    (m, 8H),                                                                 4.0  (s, 3H)                                   79    m-CF.sub.3 3-F  5-F CH.sub.3                                                                           8.50˜6.60                                                                    (m, 8H),                                                                 3.95 (s, 3H)                                   80    m-CF.sub.3 OCFHCF.sub.2 O                                                                4-CF.sub.3                                                                         H   CH.sub.3                                                                           8.6˜7.15                                                                     (m, 9H),                                                                 6.5˜5.4                                                                      (d, t 1H),                                                               3.95 (s, 3H)                                   81    m-CF.sub.2 BrO                                                                           4-CF.sub.3                                                                         H   CH.sub.3                                                                           8.6˜7.2                                                                      (m, 9H),                                                                 3.95 (s, 3H)                                   82    m-CF.sub.2 BrCF.sub.2 O                                                                  4-CF.sub.3                                                                         H   CH.sub.3                                                                           8.65˜8.40                                                                    (m, 3H),                                                                 8.25˜8.0                                                                     (m, 2H),                                                                 7.85˜ 7.2                                                                    (m, 4H),                                                                 4.0  (s, 3H)                                   83    m-CF.sub.2 HCF.sub.2 O                                                                   4-CF.sub.3                                                                         H   CH.sub.3                                                                           8.7˜7.2                                                                      (m, 9H),                                                                 6.85 (t, 0.25H),                                                              5.95 (t, 0.5H),                                                               5.05 (t, 0.25H),                                                              3.95 (s, 3H)                                   __________________________________________________________________________     *Solvent: CDCl.sub.3 + DMSOd.sub.6                                       

The compound represented by the formula (IV) is prepared by reacting acompound of the formula: ##STR12## [wherein R' is a methoxymethoxy groupat the ortho or meta position; and R², R³ and R⁴ are each as definedabove] with an acid. The reaction is usually carried out with a solventat a temperature of 20° to 100° C. for a period of 1 to 5 hours.

Normally, the acid is used in an amount of 1 to 10 equivalents to oneequivalent of the compound (I-5).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chlorobenzene,dichlorobenzene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), ketones(e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone,cyclohexanone), alcohols (e.g., methanol, ethanol, isopropanol,t-butanol), water, and mixtures thereof.

The acid includes organic acids (e.g., acetic acid), inorganic acids(e.g., hydrochloric acid, sulfuric acid), and Lewis acids (e.g.,fluoroborane ether complex).

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,recrystallization, etc. to obtain the desired compound.

PRODUCTION EXAMPLE 7

8 g of 2-(4-fluorophenyl)-4-(3-methoxymethoxyphenyl)-5-methoxypyrimidinewas added to a mixture of 150 ml of tetrahydrofuran and 150 ml ofisopropyl alcohol. After adding 10 ml of 12N hydrochloric acid thereto,the mixture was stirred for 3 hours at 60° C. The solvent was distilledaway under reduced pressure. The residue was washed with water, and thendried to obtain 7 g of2-(fluorophenyl)-4-(3-hydroxyphenyl)-5-methoxypyrimidine.

The compounds, which are used as a starting material for the compoundsof the present invention, can be produced by the following procedures:

Procedure (a)

The compound (II-1) is prepared by reacting a compound of the formula(VIII-1): ##STR13## [wherein R¹ is as defined above] with a compound ofthe formula (IX-1): ##STR14## [wherein R² and R³ are each as definedabove].

The reaction is usually carried out in a solvent at a temperature ofabout 20° to 100° C. for a period of about 0.5 to 5 hours.

Normally, the compound (IX-1) is used in an amount of about 1.1 to 1.2equivalents to one equivalent of the compound (VIII-1).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chlorobenzene,dichlorobenzene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), alcohols(e.g., methanol, ethanol, isopropanol), acid amides (e.g.,N,N-dimethylformamide, acetamide), sulfur compounds (e.g., dimethylsulfoxide, sulfolane), and mixtures thereof.

In the above reaction, the compound (IX-1) is normally used in the formof adducts of acids (e.g., a salt of hydrochloric acid). In this case,inorganic bases (e.g., potassium carbonate) or alkali metal alkoxides(e.g., sodium methoxide, sodium ethoxide) are used.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,recrystallization, etc.

Further, the benzamidine derivative represented by the formula (IX-1) iseither a well known compound or produced by an ordinary method.

Procedure (b)

The compound represented by the formula (VIII-1) is prepared by reactinga compound of the formula (X): ##STR15## [wherein R¹ is as definedabove] with N,N-dimethylformamide dimethylacetal. The reaction isusually carried out with or without a solvent at a temperature of 20° to150° C. for a period of about 0.5 to 10 hours.

Normally, N,N-dimethylformamide dimethylacetal is used in an amount of1.0 to 1.5 equivalents to one equivalent of the compound (X).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chloroform, carbontetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers(e.g., diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran,diethylene glycol dimethyl ether), alcohols (e.g., methanol, ethanol,isopropanol, t-butanol, octanol, cyclohexanol, methylcellosolve,diethylene glycol, glycerin), acid amides (e.g., N,N-dimethylformamide),sulfur compounds (e.g., dimethyl sulfoxide, sulfolane), and mixturesthereof.

The derivative represented by the formula (X) may be produced by amethod described, for example, in J. Org. Chem., 29, 2329 (1964); J. Am.Chem. Soc., 77, 5063 (1955); J. Org. Chem., 28, 1896 (1963). Thederivative represented by the formula (X) is produced in the presence ofsodium hydroxide.

Procedure (c)

The compound (II-1)' is prepared by reacting a compound of the formula(II-2): ##STR16## [wherein R¹¹ represents a hydrogen atom, or a halogenatom, a (C₁ to C₃)-alkyl group, a halo-(C₁ to C₃)-alkyl group, a (C₁ toC₆)-alkoxy group, a (C₂ to C₆)-alkynyloxy group, a (C₂ to C₆)-alkenyloxygroup, a halo-(C₂ to C₆)-alkynyloxy group, a halo-(C₂ to C₆)-alkenyloxygroup, a halo-(C₁ to C₆)-alkoxy group, a phenoxy group or a (C₁ toC₂)-alkoxy-(C₁ to C₂)-alkoxy group, at the ortho or meta position; R²²and R³³, which may be either the same or different, each represents ahydrogen atom, a halogen atom, a (C₁ to C₂)-alkyl group, a halo-(C₁ toC₂)-alkyl group, a (C₁ to C₂)-alkoxy group, or a halo-(C₁ to C₂)-alkoxygroup; provided that R¹¹, R²² and R³³ are not a hydrogen atom at thesame time and that both of R²² and R³³, if each representing asubstituent other than a hydrogen atom, are not at the ortho positionfor the pyrimidine ring at the same time with a compound of the formula:##STR17##

The reaction is usually carried out in a solvent at a temperature ofabout 0° to 40° C. for a period of about 0.5 to 10 hours. Themeta-chloroperbenzoic acid is used in an amount of 2 to 3 mol per mol ofthe pyrimidine derivative represented by the formula (II-2).

The solvent includes halogenated hydrocarbons (e.g., chloroform, carbontetrachloride, dichloroethane, chlorobenzene, dichlorobenzene).

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,recrystallization, etc. to obtain the target compound of the invention.

Procedure (d)

The compound (II-2) is prepared by reacting a compound of the formula(VIII-2): ##STR18## [wherein R¹¹ is as defined above] with a compound ofthe formula (IX-2): ##STR19## [wherein R²² and R³³ are each as definedabove].

The reaction is usually carried out in a solvent at a temperature ofabout 20° to 100° C. for a period of about 2 to 10 hours.

Normally, the compound (IX-2) is used in an amount of about 1.1 to 2.0equivalents to one equivalent of the compound (VIII-2).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane,ligroin, petroleum ether), aromatic hydrocarbons (e.g., benzene,toluene, xylene), halogenated hydrocarbons (e.g., chlorobenzene,dichlorobenzene), ethers (e.g., diethyl ether, diisopropyl ether,dioxane, tetrahydrofuran, diethylene glycol dimethyl ether), alcohols(e.g., methanol, ethanol, isopropanol), acid amides (e.g.,N,N-dimethylformamide, acetamide), sulfur compounds (e.g., dimethylsulfoxide, sulfolane), and mixtures thereof.

In the above reaction, the compound (IX-2) is normally used in the formof adducts of acids (e.g., a salt of hydrochloric acid). In this case,inorganic bases (e.g., potassium carbonate) or alkali metal alkoxides(e.g., sodium methoxide, sodium ethoxide) are used.

After completion of the reaction, the reaction mixture is subjected tothe usual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,recrystallization, etc.

Further, the benzamidine derivative represented by the formula (IX-2) iseither a well known compound or produced by an ordinary method.Procedure (e):

The compound (VIII-2) is prepared by reacting a compound of the formula(VIII-3): ##STR20## [wherein R¹¹ is as defined above and R⁴⁴ is a (C₁ toC₃)-alkoxy group] with a compound of the formula:

    CH.sub.3 I

The reaction is usually carried out in a solvent in the presence of abase at a temperature of 0° to 50° C. for 0.5 to 10 hours. Methyl iodideis used in an amount of about 1.5 mol while the base is used in anamount of about 1.0 to 1.2 mol each per mol of the ethane derivative ofthe formula (VIII-3).

The solvent includes alcohols (e.g., methanol, ethanol, isopropanol).Examples of the base include sodium hydroxide, potassium hydroxide,sodium carbonate and potassium carbonate.

After completion of the reaction, the reaction mixture is neutralizedwith an acid and subjected to the usual after-treatment such asextraction with organic solvents, concentration, etc., and if necessary,purified by chromatography, distillation, etc. Thus the target compoundof the present invention can be obtained.

Procedure (f)

The compound (VIII-3) is prepared by reacting a compound of the formula(XI): ##STR21## [wherein R¹¹ is as defined above] with a compound of theformula (XII): ##STR22## [wherein R⁴⁴ is as defined above and X is abromine atom or a chlorine atom].

The reaction is usually carried out either without using any solvent orin a solvent in the presence of a base at a temperature of 0° to 40° C.for 0.1 to 5 hours. The alkoxycarbonylsulfenyl halide of the formula(XII) is used in an amount of 1.0 to 1.5 mol while the base is used inan amount of 1.2 to 2.0 mol each per mol of the ethene derivative of theformula (XI).

The solvent includes aliphatic hydrocarbons (e.g., hexane, heptane) andaromatic hydrocarbons (e.g., benzene, toluene, xylene). Examples of thebase include pyridine, triethylamine, etc.

After completion of the reaction, the reaction mixture is treated withan aqueous solution of sodium hydrogencarbonate and subjected to theusual after-treatment such as extraction with organic solvents,concentration, etc., and if necessary, purified by chromatography,distillation, etc. Thus the target compound of the present invention canbe obtained.

The 1-(N,N-dimethylamino)-2-benzoylethene derivative represented by theformula (XI) and the alkoxycarbonylsulfenyl halide represented by theformula (XII) may be respectively produced by methods described, forexample, in Chem. Ber., 97, 3397 (1964) and Angew. Chem. Internat.Edit., 9, 54 (1970).

Examples of Compound (II) {(II-1), (II-1)' and (II-2)} which can beproduced by the procedures (a), (c) and (d) include those shown in Table3. However, it is a matter of course that the present invention is notrestricted thereby.

                  TABLE 3                                                         ______________________________________                                         ##STR23##                    (II)                                            R.sup.1        R.sup.2   R.sup.3  W.sup.1                                     ______________________________________                                        H              4-Cl      H        CH.sub.3 SO.sub.2                           H              4-Br      H        CH.sub.3 SO.sub.2                           H              4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           H              4-NO.sub.2                                                                              H        CH.sub.3 SO.sub.2                           m-F            H         H        CH.sub.3 SO.sub.2                           m-F            4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-F            4-F       H        CH.sub.3 SO.sub.2                           m-F            4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-F            4-Cl      H        CH.sub.3 SO.sub.2                           m-F            4-Br      H        CH.sub.3 SO.sub.2                           m-Cl           4-F       H        CH.sub.3 SO.sub.2                           m-Cl           H         H        CH.sub.3 SO.sub.2                           m-Cl           4-Cl      H        CH.sub.3 SO.sub.2                           m-Cl           4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-Br           H         H        CH.sub.3 SO.sub.2                           m-Br           4-Cl      H        CH.sub.3 SO.sub.2                           m-Br           4-Br      H        CH.sub.3 SO.sub.2                           m-Br           4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-Br           4-NO.sub.2                                                                              H        CH.sub.3 SO.sub.2                           o-Br           4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-I            4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-I            4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3     4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           o-CH.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3     H         H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-Cl      H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-Br      H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-CH.sub.3 O                                                                            H        CH.sub.3 SO.sub.2                           m-CF.sub.3     3-CH.sub.3 O                                                                            H        CH.sub.3 SO.sub.2                           m-CF.sub.3     3-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3     2-F       H        CH.sub.3 SO.sub.2                           o-CF.sub. 3    4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           o-CF.sub.3     2-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 O   4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 O   4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       4-F       H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     4-F       H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              4-F       H        CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.3 S   4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 S   4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-Cl      H        CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  4-F       H        CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 O                                                                        4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 O                                                                        4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      4-F       H        CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 S   4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 S   4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            4-F       H        CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CClFHCClFO   4-F       H        CH.sub.3 SO.sub.2                           m-CClFHCClFO   4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 CO.sub.2                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.3 CH.sub.2 SO.sub.3                                                                 4-F       H        CH.sub.3 SO.sub.2                           m-CH.sub.3 CH.sub.2 SO.sub.3                                                                 4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 SO.sub.3                                                                 4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 SO.sub.3                                                                 4-CF.sub.3                                                                              H        CH.sub.3 SO.sub. 2                          m-CF.sub.3 O   4-CF.sub.3 O                                                                            H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-CF.sub.3 O                                                                            H        CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-SCH.sub.3                                                                             H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-SCH.sub.3                                                                             H        CH.sub.3 SO.sub.2                           m-CN           4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CN           4-F       H        CH.sub.3 SO.sub.2                           m-COOCH.sub.3  4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-COOCH.sub.3  4-F       H        CH.sub.3 SO.sub.2                           m-CClFCFO      4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-SCF.sub.3                                                                             H        CH.sub.3 SO.sub.2                           m-CF.sub.3     4-SCF.sub.3                                                                             H        CH.sub.3 SO.sub.2                           H              4-F       H        CH.sub.3 SO.sub.2                           H              3-F       H        CH.sub.3 SO.sub.2                           H              3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           H              4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-F            3-F       H        CH.sub.3 SO.sub.2                           m-F            3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-Cl           3-F       H        CH.sub.3 SO.sub.2                           m-Cl           3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-Cl           4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3     3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       H         H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       3-F       H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       4-Cl      H        CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     H         H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     4-Cl      H        CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   H         H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 O   4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           OCF.sub.3      H         H        CH.sub.3 SO.sub.2                           OCF.sub.3      4-F       H        CH.sub.3 SO.sub.2                           OCF.sub.3      3-F       H        CH.sub.3 SO.sub.2                           OCF.sub.3      3-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           OCF.sub.3      4-Cl      H        CH.sub.3 SO.sub.2                           OCF.sub.3      4-CH.sub.3                                                                              H        CH.sub.3 SO.sub.2                           H              2-F       4-Cl     CH.sub.3 SO.sub.2                           H              3-F       4-Cl     CH.sub.3 SO.sub.2                           H              2-F       4-Br     CH.sub.3 SO.sub.2                           H              3-F       4-F      CH.sub.3 SO.sub.2                           H              2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           H              3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-F            2-F       4-F      CH.sub.3 SO.sub.2                           m-F            3-F       4-F      CH.sub.3 SO.sub.2                           m-F            2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-F            3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-F            2-F       4-Cl     CH.sub.3 SO.sub.2                           m-F            3-F       4-Cl     CH.sub.3 SO.sub.2                           m-F            2-F       4-Br     CH.sub.3 SO.sub.2                           m-F            3-F       4-Br     CH.sub.3 SO.sub.2                           m-Cl           2-F       4-F      CH.sub.3 SO.sub.2                           m-Cl           3-F       4-F      CH.sub.3 SO.sub.2                           m-Cl           2-F       4-Cl     CH.sub.3 SO.sub. 2                          m-Cl           3-F       4-Cl     CH.sub.3 SO.sub.2                           m-Cl           2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-Cl           3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           o-Br           2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           o-Br           3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-I            2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-I            3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-I            2-F       4-F      CH.sub.3 SO.sub.2                           m-I            3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3     2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3     3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           o-CH.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           o-CH.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3     3-F       5-F      CH.sub.3 SO.sub.2                           m-CF.sub.3     2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3     3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3     2-F       4-Cl     CH.sub.3 SO.sub.2                           m-CF.sub.3     3-F       4-Cl     CH.sub.3 SO.sub.2                           m-CF.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3     3-CF.sub.3                                                                              4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3     3-Cl      4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 O   2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 O   3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 O   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 O   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 O                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       2-F       4-F      CH.sub.3 SO.sub.2                           m-(i)C.sub.3 H.sub.7 O                                                                       3-F       4-F      CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     2-F       4-F      CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       4-F      CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.2 CHCH.sub.2 O                                                                      3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              2-F       4-F      CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              3-F       4-F      CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CHCCH.sub.2 O                                                                              3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 S   2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 S   3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 S   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 S   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 O   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-CF.sub.3                                                                              4-F      CH.sub.3 SO.sub.2                           m-CF.sub. 3 O  2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 O   2-F       4-Cl     CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-F       4-Cl     CH.sub.3 SO.sub.2                           m-CF.sub.3 O   3-Cl      4-F      CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  2-F       4-F      CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  3-F       4-F      CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CCl.sub.3 O  3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 HO  3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 ClO 3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 O                                                                        2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 O                                                                        3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub. 3 CF.sub.2 O                                                                       2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 O                                                                        3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 HCF.sub.2 O                                                                       3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      2-F       4-F      CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      3-F       4-F      CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CCl.sub.2 HCF.sub.2 O                                                                      3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 S   2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 S   3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 S   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 S   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.6 H.sub.5 O                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 CO.sub.2                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            2-F       4-F      CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            3-F       4-F      CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CClFHCF.sub.2 O                                                                            3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CClFHCClFO   2-F       4-F      CH.sub.3 SO.sub.2                           m-CClFHCClFO   3-F       4-F      CH.sub.3 SO.sub.2                           m-CClFHCClFO   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CClFHCClFO   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 CO.sub.2                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 CO.sub.2                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 OCH.sub.2 O                                                                       3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.3 SO.sub.3                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 SO.sub.3                                                                   2-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 SO.sub.3                                                                   3-F       4-F      CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 SO.sub.3                                                                   2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-C.sub.2 H.sub.5 SO.sub.3                                                                   3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 SO.sub.3                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub. 3 CF.sub.2 SO.sub.3                                                                2-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 SO.sub.3                                                                 3-F       4-F      CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 SO.sub.3                                                                 2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.3 CF.sub.2 SO.sub.3                                                                 3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          2-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          3-F       4-F      CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CH.sub.2 NH.sub.2                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CN           2-F       4-F      CH.sub.3 SO.sub.2                           m-CN           3-F       4-F      CH.sub.3 SO.sub.2                           m-CN           2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CN           3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-COOCH.sub.3  2-F       4-F      CH.sub.3 SO.sub.2                           m-COOCH.sub.3  3-F       4-F      CH.sub.3 SO.sub.2                           m-COOCH.sub.3  2-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-COOCH.sub.3  3-F       4-CF.sub.3                                                                             CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.2 BrO 4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.2 BrCF.sub.2 O                                                                      4-F       H        CH.sub. 3 SO.sub.2                          m-CF.sub.2 BrCF.sub.2 O                                                                      4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-CF.sub.3 OCFHCF.sub.2 O                                                                    4-F       H        CH.sub.3 SO.sub.2                           m-CF.sub.3 OCFHCF.sub.2 O                                                                    4-CF.sub.3                                                                              H        CH.sub.3 SO.sub.2                           m-Br           H         H        CH.sub.3 S                                  m-Br           4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-Br           4-Cl      H        CH.sub.3 S                                  m-Br           4-Br      H        CH.sub.3 S                                  o-Br           4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CH.sub.3     4-F       H        CH.sub.3 S                                  m-CH.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 S                                  o-CH.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3     4-CH.sub.3 O                                                                            H        CH.sub.3 S                                  m-CF.sub.3     3-CH.sub.3 O                                                                            H        CH.sub.3 S                                  o-CF.sub.3     2-F       H        CH.sub.3 S                                  m-CF.sub.2 ClO 4-F       H        CH.sub.3 S                                  m-CF.sub.2 ClO 4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        4-F       H        CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          4-F       H        CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       4-F       H        CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3 O   4-CF.sub.3 O                                                                            H        CH.sub.3 S                                  m-CH.sub.3     2-F       4-F      CH.sub.3 S                                  o-Br           2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  o-Br           3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3     4-CF.sub.3 O                                                                            H        CH.sub.3 S                                  m-CH.sub.3     3-F       4-F      CH.sub.3 S                                  m-CH.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CH.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  o-CH.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  o-CH.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3     2-F       4-Cl     CH.sub.3 S                                  m-CF.sub.3     3-F       4-Cl     CH.sub.3 S                                  m-CF.sub.3     3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3     3-CF.sub.3                                                                              4-F      CH.sub.3 S                                  m-CF.sub.3     3-Cl      4-F      CH.sub.3 S                                  m-CH.sub.3 O   2-F       4-F      CH.sub.3 S                                  m-CH.sub.3 O   3-F       4-F      CH.sub.3 S                                  m-CH.sub.3 O   2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CH.sub.3 O   3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-C.sub.2 H.sub.5 O                                                                          2-F       4-F      CH.sub.3 S                                  m-C.sub.2 H.sub.5 O                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-C.sub.2 H.sub.5 O                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       2-F       4-F      CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     2-F       4-F      CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3 O   3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3 O   3-CF.sub.3                                                                              4-F      CH.sub.3 S                                  m-CF.sub.3 O   2-F       4-Cl     CH.sub.3 S                                  m-CF.sub.3 O   3-F       4-Cl     CH.sub.3 S                                  m-CF.sub.2 ClO 2-F       4-F      CH.sub.3 S                                  m-CF.sub.2 ClO 3-F       4-F      CH.sub.3 S                                  m-CF.sub.2 ClO 2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.2 ClO 3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        2-F       4-F      CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        3-F       4-F      CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3 CF.sub.2 O                                                                        3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.2 BrO 2-F       4-F      CH.sub.3 S                                  m-CF.sub.2 BrO 3-F       4-F      CH.sub.3 S                                  m-CF.sub.2 BrO 2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.2 BrO 3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          2-F       4-F      CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          3-F       4-F      CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-C.sub.6 H.sub.5 O                                                                          3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       2-F       4-F      CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       3-F       4-F      CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CH.sub.3 OCH.sub.2 O                                                                       3-F       4-CF.sub.3                                                                             CH.sub.3 S                                  H              4-F       3-F      CH.sub.3 S                                  H              4-F       H        CH.sub.3 S                                  H              4-CF.sub.3                                                                              H        CH.sub.3 S                                  H              3-F       H        CH.sub.3 S                                  H              3-CF.sub.3                                                                              H        CH.sub.3 S                                  H              4-Cl      H        CH.sub.3 S                                  H              4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-F            H         H        CH.sub.3 S                                  m-F            4-F       H        CH.sub.3 S                                  m-F            4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-F            3-F       H        CH.sub. 3 S                                 m-F            3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-F            4-Cl      H        CH.sub.3 S                                  m-F            4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-Cl           H         H        CH.sub.3 S                                  m-Cl           4-F       H        CH.sub.3 S                                  m-Cl           4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-Cl           3-F       H        CH.sub.3 S                                  m-Cl           3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-Cl           4-Cl      H        CH.sub.3 S                                  m-Cl           4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3     H         H        CH.sub.3 S                                  m-CF.sub.3     4-F       H        CH.sub.3 S                                  m-CF.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3     3-F       H        CH.sub.3 S                                  m-CF.sub.3     3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3     4-Cl      H        CH.sub.3 S                                  m-CF.sub.3     4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       H         H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       4-F       H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       3-F       H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       4-Cl      H        CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     H         H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     4-F       H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     4-Cl      H        CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3 O   H         H        CH.sub.3 S                                  m-CF.sub.3 O   4-F       H        CH.sub.3 S                                  m-CF.sub.3 O   4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3 O   3-F       H        CH.sub.3 S                                  m-CF.sub.3 O   3-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.3 O   4-Cl      H        CH.sub.3 S                                  m-CF.sub.3 O   4-CH.sub.3                                                                              H        CH.sub.3 S                                  o-CF.sub.3     H         H        CH.sub.3 S                                  o-CF.sub.3     4-F       H        CH.sub.3 S                                  o-CF.sub.3     4-CF.sub.3                                                                              H        CH.sub.3 S                                  o-CF.sub.3     3-F       H        CH.sub.3 S                                  o-CF.sub.3     3-CF.sub.3                                                                              H        CH.sub.3 S                                  o-CF.sub.3     4-Cl      H        CH.sub.3 S                                  o-CF.sub.3     4-CH.sub.3                                                                              H        CH.sub.3 S                                  m-C.sub.2 H.sub.5 O                                                                          4-F       H        CH.sub.3 S                                  m-C.sub.2 H.sub.5 O                                                                          4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-F            3-F       4-F      CH.sub.3 S                                  m-Cl           3-F       4-F      CH.sub.3 S                                  m-CF.sub.3     3-F       4-F      CH.sub.3 S                                  m-(i)C.sub.3 H.sub.7 O                                                                       3-F       4-F      CH.sub.3 S                                  m-(sec)C.sub.4 H.sub.9 O                                                                     3-F       4-F      CH.sub.3 S                                  m-CF.sub.3 O   3-F       4-F      CH.sub.3 S                                  m-CH.sub.3 CH.sub.2 O                                                                        3-F       4-F      CH.sub.3 S                                  H              4-Br      H        CH.sub.3 S                                  m-I            4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-I            4-F       H        CH.sub.3 S                                  m-I            2-F       4-F      CH.sub.3 S                                  m-I            2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-I            3-F       4-F      CH.sub.3 S                                  m-I            3-F       5-F      CH.sub.3 S                                  m-Cl           2-F       4-F      CH.sub.3 S                                  m-Cl           2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-Cl           3-F       5-F      CH.sub.3 S                                  m-F            4-Br      H        CH.sub.3 S                                  m-F            2-F       4-F      CH.sub.3 S                                  m-F            3-F       5-F      CH.sub. 3 S                                 m-F            2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  H              2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  H              3-F       4-F      CH.sub.3 S                                  H              3-F       5-F      CH.sub.3 S                                  m-CF.sub.3     2-F       4-F      CH.sub.3 S                                  m-CF.sub.3     2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3     3-F       5-F      CH.sub.3 S                                  m-CF.sub.3 O   2-F       4-F      CH.sub.3 S                                  m-CF.sub.3 O   2-F       4-CF.sub.3                                                                             CH.sub.3 S                                  m-CF.sub.3 O   3-F       5-F      CH.sub.3 S                                  m-CF.sub.2 BrO 4-F       H        CH.sub.3 S                                  m-CF.sub.2 BrO 4-CF.sub.3                                                                              H        CH.sub.3 S                                  m-CF.sub.2 BrCF.sub.2 O                                                                      4-F       H        CH.sub.3 S                                  m-CF.sub.2 BrCF.sub.2 O                                                                      4-CF.sub.3                                                                              H        CH.sub.3 S                                  ______________________________________                                    

PRODUCTION EXAMPLE 8 Procedure (a)

6 g of1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)etheneand 4 g of 4-fluorobenzamidine hydrochloride were dissolved in 30 ml ofmethanol at room temperature. After adding 1.2 g of sodium methoxidethereto, the mixture was heated under reflux for 1 hour. The solvent wasdistilled away under reduced pressure. The residue was washed withwater, and then dried to obtain 6 g of2-(4-fluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine(Compound 112).

PRODUCTION EXAMPLE 9 Procedure (a)

6 g of1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)etheneand 4.6 g of 2,4-difluorobenzamidine hydrochloride were dissolved in 30ml of methanol at room temperature and 1.2 g of sodium methoxide wasadded thereto. The resulting mixture was heated under reflux for anhour. The solvent was distilled away under reduced pressure. The residuewas washed with water and then dried to obtain 6 g of2-(2,4-difluorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidine(Compound 147).

PRODUCTION EXAMPLE 10 Procedure (c)

1.5 g of2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methylmercaptopyrimidinewas added to 30 ml of dichloromethane. 2.0 g of m-chloroperbenzoic acidwas added to the obtained reaction mixture under cooling in an ice-bath.Then, the resulting mixture was stirred at room temperature for 5 hours.After adding water, the mixture was extracted with dichloromethane. Theorganic phase was successively washed with a saturated aqueous solutionof sodium sulfite and a saturated aqueous solution of sodiumhydrogencarbonate. The solvent was distilled away under reduced pressureand the residue was subjected to column chromatography. Thus 1.5 g of2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methanesulfonylpyrimidinewas obtained (Compound 113).

PRODUCTION EXAMPLE 11 Procedure (d)

2.8 g of1-methylmercapto-1-(3-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethene,2.3 g of 4-chlorobenzamidine acetate and 650 mg of sodium methoxide wereadded to 200 ml of methanol and the resulting mixture was allowed toreact under reflux for 5 hours. After completion of the reaction, thesolvent was distilled away under reduced pressure. After adding water,the residue was extracted with ethyl acetate and subjected to columnchromatography. Thus 2.5 g of2-(4-chlorophenyl)-4-(3-trifluoromethylphenyl)-5-methylmercaptopyrimidinewas obtained (Compound 150).

Table 4 illustrates examples of the compound (II) produced according tothe Production Example 8 to 11.

                  TABLE 4                                                         ______________________________________                                         ##STR24##                                                                    Com-                                                                          pound                                  .sup.1 H-NMR                           No.   R.sup.1     R.sup.2  R.sup.3                                                                            W.sup.1                                                                              (δ value)*                       ______________________________________                                        101   H           4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.55(s, 1H),                                                                  8.72-8.6(d,                                                                   2H), 8.05-                                                                    7.5(m, 7H),                                                                   3.15(s, 3H)                            102   H           4-NO.sub.2                                                                             H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.8-8.3(q,                                                                    4H), 7.7                                                                      (brs, 5H),                                                                    3.2(s, 3H)                             103   m-Cl        H        H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.65-8.45                                                                     (m, 2H),                                                                      7.8-7.45(m,                                                                   7H), 2.8(s,                                                                   3H)                                    104   m-Cl        4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.7-8.55(d,                                                                   2H), 7.85-                                                                    7.2(m, 6H),                                                                   2.8(s, 3H)                             105   m-Br        H        H    CH.sub.3 SO.sub.2                                                                    9.25(s, 1H),                                                                  8.55-7.3(m,                                                                   9H), 3.15(s,                                                                  3H)                                    106   m-Br        4-Cl     H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.55-7.5(m,                                                                   8H), 3.2(s,                                                                   3H)                                    107   m-Br        4-Br     H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.5-8.35                                                                      (d, 2H),                                                                      7.95-7.4                                                                      (m, 6H),                                                                      3.2(s, 3H)                             108   m-Br        4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.7-8.5(d,                                                                    2H), 8.0-7.4                                                                  (m, 6H), 3.2                                                                  (s, 3H)                                109   o-Br        4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.55(s, 1H),                                                                  8.65-8.5(d,                                                                   2H), 7.95-                                                                    7.35(m, 6H),                                                                  3.2(s, 3H)                             110   m-CF.sub.3  H        H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.65-7.4                                                                      (m, 9H), 2.8                                                                  (s, 3H)                                111   m-CF.sub.3  4-CH.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.5-8.35                                                                      (d, 2H),                                                                      8.05-7.85                                                                     (m, 4H),                                                                      7.45-7.3                                                                      (d, 2H), 3.15                                                                 (s, 3H), 2.4                                                                  (s, 3H)                                112   m-CF.sub.3  4-F      H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.70-7.0                                                                      (m, 8H), 3.0                                                                  (s, 3H)                                113   m-CF.sub.3  4-Cl     H    CH.sub.3 SO                                                                          9.4(s, 1H),                                                                   8.55-8.4(d,                                                                   2H), 8.0-                                                                     7.45(m,                                                                       6H), 3.0                                                                      (s, 3H)                                114   m-CF.sub.3  4-Br     H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.5-7.6                                                                       (m, 8H),                                                                      3.05(s, 3H)                            115   m-CF.sub.3  4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.75-7.6                                                                      (m, 8H), 2.8                                                                  (s, 3H)                                116   m-CF.sub.3  4-NO.sub.2                                                                             H    CH.sub.3 SO.sub.2                                                                    9.6(s, 1H),                                                                   8.8-7.7                                                                       (m, 8H),                                                                      3.25(s, 3H)                            117   m-CF.sub.3  4-CH.sub.3 O                                                                           H    CH.sub.3 SO.sub.2                                                                    9.4(s, 1H),                                                                   8.6-8.4(d,                                                                    2H), 8.1-                                                                     7.7(m, 4H),                                                                   7.1-6.95                                                                      (d, 2H), 3.9                                                                  (s, 3H), 3.0                                                                  (s, 3H)                                118   m-I         4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.75-8.6                                                                      (d, 2H),                                                                      8.15-7.2(m,                                                                   6H), 3.22                                                                     (s, 3H)                                119   m-F         H        H    CH.sub.3 SO                                                                          9.45(s, 1H),                                                                  8.55-8.35                                                                     (m, 2H),                                                                      7.75-7.55                                                                     (m, 7H),                                                                      3.1(s, 3H)                             120   m-F         4-CH.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.4-8.25(d,                                                                   2H), 7.6-7.3                                                                  (m, 6H), 3.2                                                                  (s, 3H),                                                                      2.45(s, 3H)                            121   m-F         4-F      H    CH.sub.3 SO.sub.2                                                                    9.4(s, 1H),                                                                   8.65-8.4                                                                      (m, 2H),                                                                      7.75-7.0                                                                      (m, 6H),                                                                      2.8(s, -     3H)                       122   m-F         4-Cl     H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.5-8.35                                                                      (d, 2H), 7.7-                                                                 7.5(m, 6H),                                                                   3.2(s, 3H)                             123   m-F         4-Br     H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.4-8.25                                                                      (d, 2H),                                                                      7.75-7.4                                                                      (m, 6H),                                                                      3.15(s, 3H)                            124   m-I         4-F      H    CH.sub.3 SO                                                                          9.35(s, 1H),                                                                  8.6-8.3                                                                       (m, 2H),                                                                      8.0-7.15                                                                      (m, 6H),                                                                      3.05(s, 3H)                            125   m-CF.sub.3 O                                                                              4-CF.sub.3                                                                             H    CH.sub.3 SO                                                                          9.45(s, 1H),                                                                  8.7-8.55                                                                      (d, 2H),                                                                      7.8-7.45                                                                      (m, 6H),                                                                      2.8(s, 3H)                             126   m-CF.sub.3 O                                                                              4-F      H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.7-8.45                                                                      (m, 2H),                                                                      7.75-7.0                                                                      (m, 6H),                                                                      2.8(s, 3H)                             127   o-CF.sub.3  4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.7-8.55                                                                      (m, 2H),                                                                      7.8-7.65                                                                      (m, 6H),                                                                      2.8(s, 3H)                             128   m-CH.sub.3  4-F      H    CH.sub.3 SO.sub.2                                                                    9.30(s, 1H),                                                                  8.6-6.9                                                                       (m, 8H),                                                                      2.65(s, 3H),                                                                  2.4(s, 3H)                             129   m-C.sub.2 H.sub.5 O                                                                       4-F      H    CH.sub.3 SO.sub.2                                                                    9.40(s, 1H),                                                                  8.70-8.40                                                                     (m, 2H),                                                                      7.50-6.95                                                                     (m, 6H),                                                                      4.30-3.95                                                                     (q, 2H),                                                                      2.75(s, 3H),                                                                  1.60-1.35                                                                     (t, 3H)                                130   m-CH.sub.3 OCH.sub.2 O                                                                    4-F      H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.60-8.35                                                                     (m, 2H),                                                                      7.45- 6.95                                                                    (m, 6H),                                                                      5.20(s, 2H),                                                                  3.45(s, 3H)                                                                   2.75(s, 3H)                            131   m-CF.sub.3  2-F      H    CH.sub.3 SO.sub.2                                                                    9.50(s, 1H),                                                                  8.30-7.0                                                                      (m, 8H),                                                                      2.80(s, 3H)                            132   m-C.sub.6 H.sub.5 O                                                                       4-F      H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.60-                                                                         8.35(m, 2H),                                                                  7.5-6.95                                                                      (m, 11H),                                                                     2.80(s, 3H)                            133   o-CF.sub.3  2-F      H    CH.sub.3 SO.sub.2                                                                    9.5(s, 1H),                                                                   8.20-7.0                                                                      (m, 8H),                                                                      2.80(s, 3H)                            134   m-Cl        2-F      H    CH.sub.3 SO.sub.2                                                                    9.50(s, 1H),                                                                  8.35-                                                                         7.0(m, 8H),                                                                   2.80(s, 3H)                            135   m-CF.sub.3  3-CH.sub.3 O                                                                           H    CH.sub.3 SO.sub.2                                                                    9.40(s, 1H),                                                                  8.20-                                                                         6.95(m, 8H),                                                                  3.85(s, 3H),                                                                  2.75(s, 3H)                            136   m-CF.sub.3  3-F      H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.40-                                                                         7.05(m, 8H),                                                                  2.80(s, 3H)                            137   m-CF.sub.3  3-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.85-                                                                         8.60(m, 2H),                                                                  8.10-7.40                                                                     (m, 6H),                                                                      2.75(s, 3H)                            138   m-CF.sub.3 O                                                                              3-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.30(s, 1H),                                                                  8.70-                                                                         8.50(m, 2H),                                                                  7.80-7.20                                                                     (m, 6H), 2.90                                                                 (s, 3H)                                139   m-CH.sub.3 OCH.sub.2 O                                                                    4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.50(s, 1H),                                                                  3.80-8.50                                                                     (m, 2H),                                                                      7.85-7.20                                                                     (m, 6H),                                                                      5.25(s, 2H),                                                                  3.50(s, 3H),                                                                  2.80(s, 3H)                            140   m-CF.sub.3 O                                                                              3-Cl     H    CH.sub.3 SO.sub.2                                                                    9.40(s, 1H),                                                                  8.60-8.35                                                                     (m, 2H),                                                                      7.90-7.25                                                                     (m, 6H),                                                                      2.75(s, 3H)                            141   m-CF.sub.3  4-SCH.sub.3                                                                            H    CH.sub.3 SO.sub.2                                                                    9.30(s, 1H),                                                                  8.45-7.15                                                                     (m, 8H),                                                                      2.75(s, 3H),                                                                  2.50(s, 3H)                            142   m-CH.sub.3 CH.sub.2 O                                                                     4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.60-8.45                                                                     (m, 2H),                                                                      7.70-6.95                                                                     (m, 6H),                                                                      4.25-3.90                                                                     (q, 2H), 2.75                                                                 (s, 3H),                                                                      1.55-                                                                         1.30(t, 3H)                            143   m-CN        4-CF.sub.3                                                                             H    CH.sub.3 SO.sub.2                                                                    9.40(s, 1H),                                                                  8.75-7.6                                                                      (m, 8H),                                                                      3.0(s, 3H)                             144   o-CF.sub.3 O                                                                              2-F      4-F  CH.sub.3 SO.sub.2                                                                    9.40(s, 1H),                                                                  8.45-6.70                                                                     (m, 7H),                                                                      2.80(s, 3H)                            145   m-CF.sub.3 O                                                                              3-F      4-F  CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.45-7.40                                                                     (m, 7H), 3.10                                                                 (s, 3H)                                146   m-CF.sub.3 O                                                                              3-F      5-F  CH.sub.3 SO.sub.2                                                                    9.35(s, 1H),                                                                  8.20-7.10                                                                     (m, 7H),                                                                      2.60(s, 3H)                            147   m-CF.sub.3  2-F      4-F  CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.45-6.70                                                                     (m, 7H),                                                                      2.75(s, 3H)                            148   m-CF.sub.3  3-F      4-F  CH.sub.3 SO.sub.2                                                                    9.50(s, 1H),                                                                  8.55-7.05                                                                     (m, 7H),                                                                      2.75(s, 3H)                            149   m-CF.sub.3  3-F      5-F  CH.sub.3 SO.sub.2                                                                    9.45(s, 1H),                                                                  8.25-6.75                                                                     (m, 7H),                                                                      2.75(s, 3H)                            150   m-CF.sub.3  4-Cl     H    CH.sub.3 S                                                                           8.7-7.2                                                                       (m, 9H),                                                                      2.5(s, 3H)                             151   o-CF.sub.3  4-Cl     H    CH.sub.3 S                                                                           8.75-7.25                                                                     (m, 9H),                                                                      2.5(s, 3H)                             ______________________________________                                         *Solvent                                                                      CDCl.sub.3 : Compounds 104, 110, 112, 121, 125, 126, 127, 129 to 141          CDCl.sub.3 + DMSOd.sub.6 : Compounds 113, 117, 128, 142 to 151                DMSO-d.sub.6 : other compounds                                           

Examples of the compounds (VIII) {(VIII-1), (VIII-2) and (VIII-3)} whichcan be produced by the procedures (b), (e), (f) include those shown inTable 5. However, it is a matter of course that the present invention isnot restricted thereby.

                  TABLE 5                                                         ______________________________________                                         ##STR25##                                                                    R.sup.1              W.sup.2                                                  ______________________________________                                        H                    SCOOCH.sub.3                                             H                    SCOOC.sub.2 H.sub.5                                      m-F                  SCOOCH.sub.3                                             m-F                  SCOOC.sub.2 H.sub.5                                      m-Cl                 SCOOCH.sub.3                                             m-Cl                 SCOOC.sub.2 H.sub.5                                      m-Br                 SCOOCH.sub.3                                             m-Br                 SCOOC.sub.2 H.sub.5                                      m-CF.sub.3           SCOOCH.sub.3                                             m-CF.sub.3           SCOOC.sub.2 H.sub.5                                      m-CH.sub.3 O         SCOOCH.sub.3                                             m-CH.sub.3 O         SCOOC.sub.2 H.sub.5                                      m-C.sub.2 H.sub.5 O  SCOOCH.sub.3                                             m-C.sub.2 H.sub.5 O  SCOOC.sub.2 H.sub.5                                      ______________________________________                                        R.sup.11             R.sup.5                                                  ______________________________________                                        m-(i)C.sub.3 H.sub.7 O                                                                             SCOOCH.sub.3                                             m-(i)C.sub.3 H.sub.7 O                                                                             SCOOC.sub.2 H.sub.5                                      m-(sec)C.sub.4 H.sub.9 O                                                                           SCOOCH.sub.3                                             m-(sec)C.sub.4 H.sub.9 O                                                                           SCOOC.sub.2 H.sub.5                                      m-CH.sub.3           SCOOCH.sub.3                                             o-CH.sub.3           SCOOCH.sub.3                                             m-CF.sub.3 O         SCOOCH.sub.3                                             m-CF.sub.3 O         SCOOC.sub.2 H.sub.5                                      o-Br                 SCOOCH.sub.3                                             o-Br                 SCOOC.sub.2 H.sub.5                                      o-CF.sub.3           SCOOCH.sub.3                                             o-CF.sub.3           SCOOC.sub.2 H.sub.5                                      m-CF.sub.3 O         SCOOC.sub.3 H.sub.7                                      m-CF.sub.3           SCOOC.sub.3 H.sub.7                                      m-C.sub.6 H.sub.5 O  SCOOCH.sub.3                                             m-CH.sub.3 OCH.sub.2 O                                                                             SCOOCH.sub.3                                             m-I                  SCOOCH.sub.3                                             m-CF.sub.2 ClO       SCOOCH.sub.3                                             m-CF.sub.3 CF.sub.2 O                                                                              SCOOCH.sub.3                                             m-CF.sub.2 BrO       SCOOCH.sub.3                                             m-CF.sub.2 BrCF.sub.2 O                                                                            SCOOCH.sub.3                                             H                    SCH.sub.3                                                m-F                  SCH.sub.3                                                m-Cl                 SCH.sub.3                                                m-Br                 SCH.sub.3                                                m-CF.sub.3           SCH.sub.3                                                m-CH.sub.3 O         SCH.sub.3                                                m-C.sub.2 H.sub.5 O  SCH.sub.3                                                m-(i)C.sub.3 H.sub.7 O                                                                             SCH.sub.3                                                m-(sec)C.sub.4 H.sub.9 O                                                                           SCH.sub.3                                                m-CF.sub.3 O         SCH.sub.3                                                o-Br                 SCH.sub.3                                                o-CF.sub.3           SCH.sub.3                                                m-CH.sub.3           SCH.sub.3                                                m-C.sub.6 H.sub.5 O  SCH.sub.3                                                m-CH.sub.3 OCH.sub.2 O                                                                             SCH.sub.3                                                m-I                  SCH.sub.3                                                m-CF.sub.2 ClO       SCH.sub.3                                                m-CF.sub.3 CF.sub.2 O                                                                              SCH.sub.3                                                m-CF.sub.2 BrO       SCH.sub.3                                                m-CF.sub.2 BrCF.sub.2 O                                                                            SCH.sub.3                                                ______________________________________                                    

PRODUCTION EXAMPLE 12 Procedure (b)

2.5 g of m-trifluoromethyl-α-methanesulfonylacetophenone and 1.4 g ofN,N-dimethylformamide dimethylacetal were dissolved in 40 ml of toluene,and the resulting mixture was heated under reflux for 2 hours. Thesolvent was distilled away under reduced pressure. The residue wastreated with column chromatography on silica gel, thereby obtaining 3 gof1-(3-trifluoromethylbenzoyl)-1-methanesulfonyl-2-(N,N-dimethylamino)ethene(Compound 205).

PRODUCTION EXAMPLE 13 Procedure (f)

4.2 g of 1-(N,N-dimethylamino)-2-(2-trifluoromethylbenzoyl)ethene and2.6 g of triethylamine were added to 50 ml of benzene. 2.4 g ofmethoxycarbonylsulfenyl chloride dissolved in 10 ml of benzene was addeddropwise to the solution obtained above under cooling in an ice-bath.After completion of the addition, the reaction mixture was stirred atroom temperature for 1 hour. After completion of the reaction, thesolvent was distilled away under reduced pressure. After adding anaqueous solution of sodium hydrogencarbonate, the mixture was extractedwith ether. Thus 5.0 g of1-methoxycarbonylthio-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethenewas obtained (Compound 209).

PRODUCTION EXAMPLE 14 Procedure (e)

5.8 g of1-methoxycarbonylthio-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)etheneand 4.2 g of methyl iodide were added to 100 ml of ethanol. 770 mg ofsodium hydroxide was added to the obtained mixture under cooling in anice-bath. Then the resulting mixture was stirred at room temperature for3 hours and then neutralized by adding acetic acid.

The solvent was distilled away and water was added to the residue. Themixture was extracted with ethyl acetate and subjected to columnchromatography. Thus 4.5 g of1-methylmercapto-1-(2-trifluoromethylbenzoyl)-2-(N,N-dimethylamino)ethenewas obtained (Compound 216).

Some examples of the compound produced by the Production Examples 12 to14 are shown in Table 6.

                  TABLE 6                                                         ______________________________________                                         ##STR26##                                                                    Compound                                                                      No.     R.sup.1     W.sup.2   .sup.1 H-NMR (δ value)*                   ______________________________________                                        201     m-F         SO.sub.2 CH.sub.3                                                                       7.8(s, 1H), 7.7-7.2(m,                                                        4H), 3.2(s, 3H), 2.8                                                          (brs, 6H)                                       202     m-Cl        SO.sub.2 CH.sub.3                                                                       7.7-7.1(m, 5H), 3.05(s,                                                       3H), 2.7(brs, 6H)                               203     m-Br        SO.sub.2 CH.sub.3                                                                       7.9-7.15(m, 5H), 3.15                                                         (s, 3H), 2.75(brs, 6H)                          204     m-I         SO.sub.2 CH.sub.3                                                                       8.15-7.1(m, 5H), 3.2(s,                                                       3H), 2.8(brs, 6H)                               205     m-CF.sub.3  SO.sub.2 CH.sub.3                                                                       8.0-7.5(m, 5H), 3.15(s,                                                       3H), 2.8(brs, 6H)                               206     o-Br        SO.sub.2 CH.sub.3                                                                       7.85-7.25(m, 5H), 3.0                                                         (brs, 9H)                                       207     m-CF.sub.3 O                                                                              SO.sub.2 CH.sub.3                                                                       7.80-7.40(m, 5H), 3.15                                                        (s, 3H), 2.75(brs, 6H)                          208     m-CH.sub.3 OCH.sub.2 O                                                                    SO.sub.2 CH.sub.3                                                                       7.70(s, 1H), 7.40-7.10                                                        (m, 4H), 5.15(s, 2H),                                                         3.40(s, 3H), 3.15(s,                                                          3H), 2.7(brs, 6H)                               209     o-CF.sub.3  SCO.sub.2 CH.sub.3                                                                      7.65-7.15(m, 5H) 3.70                                                         (s, 3H), 3.15(s, 6H)                            210     m-CF.sub.3  SCO.sub.2 CH.sub.3                                                                      7.75-7.45(m, 5H), 3.75                                                        (s, 3H), 3.25(s, 6H)                            211     m-Cl        SCO.sub.2 CH.sub.3                                                                      7.70-7.20(m, 5H), 3.75                                                        (s, 3H), 3.20(s, 6H)                            212     H           SCO.sub.2 CH.sub.3                                                                      7.70-7.25(m, 6H), 3.80                                                        (s, 3H), 3.20(s, 6H)                            213     m-CH.sub.3 O                                                                              SCO.sub.2 CH.sub.3                                                                      7.65(s, 1H), 7.35-6.85                                                        (m, 4H)3.75(s, 6H),                                                           3.20(s, 6H)                                     214     H           SCH.sub.3 7.4(m, 6H), 3.25(s,                                                           6H), 2.1(s, 3H)                                 215     m-CF.sub.3  SCH.sub.3 7.8-7.2(m, 6H), 3.25                                                          (s, 6H), 2.05(s, 3H)                            216     o-CF.sub.3  SCH.sub.3 7.7-7.1(m, 6H),                                                               3.25(s, 6H), 2.05(s, 3H)                        217     m-Cl        SCH.sub.3 7.75-7.15(m, 6H), 3.3                                                         (s, 6H),2.05(s, 3H)                             ______________________________________                                          *Solvent: CDCl.sub.3 -                                                       **Solvent: CDCl.sub.3 + DMSOd.sub.6 -                                    

For the practical use of the compound (I), it is usually formulated withconventional solid or liquid carriers or diluents as well as surfaceactive agents or auxiliary agents into conventional preparation formssuch as emulsifiable concentrates, wettable powders, suspensions andgranules. The content of the compound (I) as the active ingredient insuch preparation forms is normally within a range of about 1 to 80% byweight, preferably of about 2 to 70% by weight. Examples of the solidcarrier or diluent are fine powders or granules of kaolin clay,attapulgite clay, bentonite, terra alba, pyrophyllite, talc,diatomaceous earth, calcite, walnut shell powders, urea, ammoniumsulfate and synthetic hydrous silicate, etc. As the liquid carrier ordiluent, there may be exemplified aromatic hydrocarbons (e.g., xylene,methylnaphthalene), alcohols (e.g., isopropanol, ethylene glycol,cellosolve), ketones (e.g., acetone, cyclohexanone, isophorone), soybeanoil, cotton seed oil, dimethyl sulfoxide, N,N-dimethylformamide,acetonitrile, water, etc.)

The surface active agent used for emulsification, dispersion orspreading may be of any type, for instance, either cationic, anionic ornon-ionic. Examples of the surface active agent include alkylsulfates,alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, phosphatesof polyoxyethylenealkylaryl ethers, polyoxyethylene alkyl ethers,polyoxyethylene alkylaryl ethers, polyoxyethylene-polyoxypropylene blockcopolymer, sorbitan fatty acid esters, polyoxyethylene sorbitan fattyacid esters, etc. Examples of the auxiliary agents includeligninsulfonates, sodium alginate, polyvinyl alcohol, gum arabic, CMC(carboxymethyl cellulose), PAP (isopropyl acid phosphate), etc.

Practical embodiments of the herbicidal composition according to thepresent invention are illustratively shown in the following FormulationExamples wherein parts are by weight. The compound number of the activeingredient corresponds to the one in Table 2.

FORMULATION EXAMPLE 1

Seventy parts of Compound 8 or 17, 3 parts of calcium ligninsulfonate, 2parts of sodium laurylsulfate and 25 parts of synthetic hydrous silicateare well mixed while being powdered to obtain a wettable powder.

FORMULATION EXAMPLE 2

Ten parts of Compound 10, 18, or 20, 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 70 partsof xylene are well mixed to obtain an emulsifiable concentrate.

FORMULATION EXAMPLE 3

Two parts of Compound 12 or 23, 1 part of synthetic hydrous silicate, 2parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts ofkaolin clay are well mixed while being powdered. The mixture is thenkneaded with water, granulated and dried to obtain granules.

FORMULATION EXAMPLE 4

Twenty-five parts of Compound 20 is mixed with 3 parts ofpolyoxyethylene sorbitan monooleate, 3 parts of carboxymethyl celluloseand 69 parts of water and pulverized until the particle size of themixture becomes less than 5 microns to obtain a suspension.

The compound (I) thus formulated in any suitable preparation form isuseful for pre-emergence or post-emergence control of undesired weeds bysoil or foliar treatment as well as flood following treatment. Thesetreatments include application to the soil surface prior to or aftertransplanting, incorporation into the soil, etc. The foliar treatmentmay be effected by spraying the herbicidal composition containing thecompound (I) over the top of plants. It may also be applied directly tothe weeds if care is taken to keep the chemical off the crop foliage.

The compound (I) may be used together with any other herbicide toimprove its activity as a herbicide, and in some cases, a synergisticeffect can be expected. Further, it may be applied in combination withan insecticide, and acaricide, a nematocide, a fungicide, a plant growthregulator, a fertilizer, a soil improver, etc. Furthermore, it may beused as a herbicide applicable to agricultural plowed fields as well aspaddy fields. It is also useful as a herbicide to be employed fororchards, pasture lands, lawns, forests, non-agricultural fields, etc.

The dosage of the compound (I) may vary depending on the prevailingweather conditions, the formulation used, the prevailing season, themode of application, the soil involved, the crop and weed species, etc.Generally, however, the dosage of the active ingredient is from about 1to 8000 grams, preferably from about 5 to 2000 grams per hectare.

The herbicidal composition of the invention formulated in the form of anemulsifiable concentrate, a wettable powder or a suspension mayordinarily be employed by diluting it with water at a volume of about100 to 1000 liters per hectare, if necessary, with addition of anauxiliary agent such as a spreading agent. Examples of the spreadingagent include, in addition to the surface active agents as noted above,polyoxyethylene resin acid (ester), ligninsulfonate, abietylenic acidsalt, dinaphthylmethanedisulfonate, paraffin, etc. The compositionformulated in the form of granules may be normally applied as suchwithout dilution.

The biological data of the compound (I) as herbicides will beillustratively shown in the following Test Examples wherein thephytotoxicity to crop plants and the herbicidal activity on weeds wereobserved visually as to the degree of germination as well as the growthinhibition and rated with an index 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,the numeral "0" indicating no material difference as seen in comparisonwith the untreated plants and the numeral "10" indicating the completeinhibition or death of the test plants.

The compounds as shown in Table 7 were used for comparison.

                  TABLE 7                                                         ______________________________________                                        Compound                                                                      Code    Structural Formula   Remarks                                          ______________________________________                                                 ##STR27##           Metamitron (Commercial herbicide)                B                                                                                      ##STR28##           DSMA (Commercial herbicide)                      C                                                                                      ##STR29##           Benthiocarb (Commercial herbicide)               D                                                                                      ##STR30##           Described in J. Heterocyclic Chem., 23, 77                                    (1986)                                           ______________________________________                                    

TEST EXAMPLE 1

Cylindrical plastic pots (diameter, 10 cm; height, 10 cm) were filledwith upland field soil, and the seeds of tall morningglory andvelvetleaf were sowed therein and covered with soil. A designated amountof the test compound formulated in a wettable powder as in FormulationExample 1 was diluted with water, and the dilution was sprayed onto thesoil surface by means of a small hand sprayer at a spray volume of 1000liters per hectare. The test plants were grown in a greenhouse for 20days, and the herbicidal activity was examined. The results are shown inTable 8.

                  TABLE 8                                                         ______________________________________                                                       Herbicidal Activity                                            Compound  Dosage     Tall                                                     No.       (g/ha)     Morningglory                                                                             Velvetleaf                                    ______________________________________                                         8        2000       10         10                                            12        2000       10         --                                            16        2000       10         10                                            17        2000       10          9                                                       500       10         --                                            18        2000        9         10                                                       500       --         10                                            19        8000       10         10                                            21        2000       10         10                                            31        2000       10         10                                                       500       10         --                                            32        2000       10         10                                            34        2000       10          9                                                       500       10         --                                            58        2000       10         --                                            61        2000        9         --                                            65        2000       10         --                                            74        2000        9         --                                            75        2000        9          8                                            76        2000       10         --                                            77        2000       10         --                                            78        2000       10          9                                            A         8000        6          6                                                      2000        2          2                                            D         2000        0          0                                            ______________________________________                                    

TEST EXAMPLE 2

Cylindrical plastic pots (doameter, 10 cm; height, 10 cm) were filledwith upland field soil, and the seeds of tall morningglory, radish andvelvetleaf were sowed therein and cultivated in a greenhouse for 10days. A designated amount of the test compound formulated in anemulsifiable concentrate as in Formulation Example 2 was diluted withwater containing a spreading agent, and the dilution was sprayed overthe foliage of the test plant by means of a small hand sprayer at aspray volume of 1000 liters per hectare. The test plants were furthergrown in a greenhouse for 20 days, and the herbicidal activity wasexamined. The results are shown in Table 9.

                  TABLE 9                                                         ______________________________________                                                   Herbicidal Activity                                                Compound                                                                              Dosage                     Tall                                       No.     (g/ha)   Radish   Velvetleaf                                                                             Morningglory                               ______________________________________                                         2      500       8       8         9                                          6      2000     10       10       10                                                 500       9       --       --                                          7      2000     10       10       10                                                 500       9       9        --                                          8      2000     10       10       10                                                 500      10       9        10                                          9      500      10       10       10                                                 125       8       --       10                                         10      500       9       9        10                                                 125       9       9         9                                                  32       9       --        9                                         11      500      --       9         9                                         12      500      10       10       10                                                 125       9       9        10                                                  32      --       8        10                                         14      2000      9       10        9                                         16      500      10       9        10                                                 125       8       8        10                                         17      500       8       9        10                                                 125      --       9        10                                         18      500      10       10       10                                                 125      10       10       10                                                  32      10       9         9                                         19      2000      9       9        10                                                 500       9       9        10                                         20      500      10       9        10                                                 125       9       9         9                                                  32       9       8         9                                         21      500      10       9         9                                                 125      10       9         9                                                  32      10       9         9                                         23      500      10       8        10                                                 125       9       8         9                                         31      500      10       10        9                                                 125      10       9         9                                                  32      10       9         9                                         32      500      10       9        10                                                 125      10       9        10                                                  32      10       9         9                                         34      500      10       9        10                                                 125       9       9        10                                         47      2000     10       10       10                                                 500       9       10       10                                                 125       9       10        9                                         48      2000     10       9        10                                                 500      10       9        10                                                 125      10       9        10                                         49      2000     10       10       10                                                 500      10       9        10                                                 125      10       9        10                                         52      2000      9       --        9                                         58      2000     10       9        10                                                 500       9       9        10                                         60      2000      9       9        --                                                 500       9       9        --                                         61      500      10       9        10                                                 125       9       9        10                                                  32       9       8        10                                         62      500       9       9        10                                                 125       9       9         9                                         63      500       9       8        10                                                 125       9       8         9                                                  32       9       8         9                                         64      2000      9       9         9                                                 500       9       9         9                                         65      500      10       9        10                                                 125      10       9        10                                                  32      10       9        10                                         66      500       9       9        10                                                 125       9       9        10                                                  32       9       9         9                                         74      2000      9       9         9                                                 500      10       9        10                                                 125      10       --        9                                         75      2000     10       9        10                                                 500      10       9        10                                                 125       9       9        10                                         76      2000     10       10       10                                                 500       9       10       10                                                 125      --       10       10                                         77      2000     10       9         9                                                 500      10       8         9                                                 125      10       8         9                                         78      2000     10       9        --                                                 500      10       9        10                                                 125      10       8         9                                         79      2000      8       10       10                                                 500      --       10       10                                                 125      --       8        10                                         B       8000      9       0         0                                                 2000      8       0         0                                         D       2000      3       2        --                                         ______________________________________                                    

TEST EXAMPLE 3

Cylindrical plastic pots (diameter, 8 cm; height, 12 cm) were filledwith paddy field soil, and the seeds of barnyardgrass (Echinochloaoryzicola) were sowed in 1 to 2 cm depth, and water was poured thereinto make a flooded condition.

Five days (at that time weeds began to germinate) thereafter, adesignated amount of the test compound formulated in an emulsifiableconcentrate as in Formulation Example 2 and diluted with water (5 ml)was applied to the pots by perfusion. The test plants were grown for anadditional 20 days in a greenhouse, and the herbicidal activity wasexamined. The results are shown in Table 10.

                  TABLE 10                                                        ______________________________________                                        Compound      Dosage  Herbicidal Activity                                     No.           (g/ha)  Banyardgrass                                            ______________________________________                                         2            4000    10                                                       4            4000    10                                                       6            4000    10                                                       7            4000    10                                                       8            4000    10                                                       9            4000    10                                                      10            4000    10                                                      11            4000    10                                                      12            4000    10                                                      13            4000    10                                                      14            4000    10                                                      15            4000    10                                                      16            4000    10                                                      17            4000    10                                                      18            4000    10                                                      19            4000    10                                                      20            4000    10                                                      21            4000    10                                                      23            4000    10                                                      31            4000    10                                                      32            4000    10                                                      34            4000    10                                                      47            4000    10                                                      48            4000    10                                                      49            4000    10                                                      52            4000    10                                                      58            4000    10                                                      61            4000    10                                                      62            4000    10                                                      64            4000    10                                                      65            4000    10                                                      66            4000    10                                                      74            4000    10                                                      75            4000    10                                                      76            4000    10                                                      77            4000    10                                                      78            4000    10                                                      79            4000    10                                                      D             4000     0                                                      ______________________________________                                    

TEST EXAMPLE 4

Wagner's pots (1/5000 are) were filled with paddy field soil, and theseeds of barnyardgrass (Echinochloa oryzicola), broad-leaved weeds(i.e., common falsepimpernel, indian toothcup, waterwort), waternutgrass and hardstem bulrush were sowed in 1 to 2 cm depth. Water waspoured therein to make a flooded condition, and rice seedlings of 3-leafstage and tubers of water nutgrass were transplanted therein, and thetest plants were grown in a greenhouse. Five days (at that timebarnyardgrass began to germinate) thereafter, a designated amount of thetest compound formulated in an emulsifiable concentrate as inFormulation Example 2 and diluted with water (10 ml) was applied to thepots by perfusion. The test plants were grown for an additional 20 daysin the greenhouse, and the herbicidal activity was examined. The resultsare shown in Table 11. At the time of the treatment, the depth of waterin the pots was kept at 4 cm and following two days, water was let leaka volume corresponding to a 3 cm depth per day.

                                      TABLE 11                                    __________________________________________________________________________                     Herbicidal Activity                                          Compound                                                                            Dosage                                                                            Phytotoxicity                                                                        Barnyard-                                                                           Broad-leaved                                                                         Hardstem                                                                           Water                                      No.   (g/ha)                                                                            Rice Plant                                                                           grass Weeds  Bulrush                                                                            Nutgrass                                   __________________________________________________________________________    18    250 3      10    10     10   10                                                63 0      10    10     10   10                                         19    250 1      10    10      9   10                                                63 0      10    10      8    9                                         21    250 2      10    10     10   10                                                63 0      10    10     10   10                                         C     250 0       4     0      0    0                                                63 0       0     0      0    0                                         __________________________________________________________________________

TEST EXAMPLE 5

Vats (area: 33×23 cm², depth: 11 cm) were filled with field soil, andthe seeds of soybean, corn, rice, velvetleaf, redroot pigweed, greenfoxtail and barnyardgrass were sowed therein and covered with soil of 1to 2 cm in thickness. A designated amount of the test compoundformulated in an emulsifiable concentrate as in Formulation Example 2was diluted with water, and the dilution was sprayed onto the soilsurface by means of a small hand sprayer at a spray volume of 1000liters per hectare. The test plants were grown in a green house for 20days, and then herbicidal activity and phytotoxicity were examined. Theresults are shown in Table 12.

                                      TABLE 12                                    __________________________________________________________________________               Phytotoxicity                                                                            Herbicidal Activity                                     Compound                                                                             Dosage                                                                            Soy-       Velvet-                                                                            Redroot                                                                             Green                                                                             Barnyard-                                No.    (g/ha)                                                                            bean                                                                              Corn                                                                             Rice                                                                              leaf pigweed                                                                             Foxtail                                                                           grass                                    __________________________________________________________________________    18     250 2   0  1   10   10    10  9                                               125 0   0  0   8    10    10  8                                        31     250 1   2  1   10   10    10  10                                              125 0   0  0   9    10    10  9                                        D      250 0   0  0   0     0     0  0                                        __________________________________________________________________________

TEST EXAMPLE 6

Vats (area: 33×23 cm², depth: 11 cm) were filled with field soil, andseeds of wheat, common chickweed, persian speedwell, field pansy, annualbluegrass and blackgrass were sowed therein and covered with soil of 1to 2 cm in thickness. A designated amount of the test compoundformulated in an emulsifiable concentrate as in Formulation Example 2was diluted with water, and the dilution was sprayed onto the soilsurface by means of a small hand sprayer at a spray volume of 1000liters per hectare. The test plants were grown in a green house for 27days and then herbicidal activity and phytotoxicity were examined. Theresults are shown in Table 13.

                                      TABLE 13                                    __________________________________________________________________________              Phyto-                                                                             Herbicidal Activity                                            Compound                                                                            Dosage                                                                            toxicity                                                                           Common                                                                              Persian                                                                             Field                                                                             Annual                                         No.   (g/ha)                                                                            Wheat                                                                              Chickweed                                                                           Speedwell                                                                           Pansy                                                                             Bluegrass                                                                          Blackgrass                                __________________________________________________________________________    18    250 1    10    10    8   10   8                                         31    250 0    10    10    8   10   8                                         D     250 0     0     0    0    0   0                                         __________________________________________________________________________

TEST EXAMPLE 7

Vats (area: 33×23 cm³, depth: 11 cm) were filled with field soil, andseeds of wheat, persian speedwell, wild mustard and field pansy weresowed therein and grown for 31 days. A designated amount of the testcompound formulated in an emulsifiable concentrate as in FormulationExample 2 was diluted with water, and the dilution was uniformly sprayedonto the whole of the stems and leaves of the plants by means of a smallhand sprayer at a spray volume of 1000 liters per hectare. The growth ofweeds and crops varied depending upon a kind of plant. During the one tofour leafstages, the height of these plants ranged from 3 to 25 cm. 25days after the treatment, the herbicidal activity and phytotoxicity wereexamined. The results are shown in Table 14. The procedures wereeffected throughout the test period in a greenhouse.

                  TABLE 14                                                        ______________________________________                                                  Phyto- Herbicidal Activity                                          Compound                                                                              Dosage  toxicity Persian  Wild   Field                                No.     (g/ha)  Wheat    Speedwell                                                                              Mustard                                                                              Pansy                                ______________________________________                                        31      250     1        10       9      9                                            125     0        9        9      9                                    D       250     0        0        0      0                                    ______________________________________                                    

While the invention has been described in detail and with reference tospecific embodiments thereof, it will be apparent to one skilled in theart that various changes and modifications can be made therein withoutdeparting from the spirit and scope thereof.

What is claimed is:
 1. A compound of the formula: ##STR31## wherein R¹represents a halo-(C₁ to C₆)-alkoxy group at the ortho or meta position,R² and R³, which may be either the same or different, each represents ahydrogen atom, a halogen atom, a (C₁ to C₂)-alkyl group, a halo-(C₁ toC₂)-alkyl group, a (C₁ to C₂)-alkoxy group, a nitro group, a (C₁ toC₂)-alkylthio group, a halo-(C₁ to C₂)-alkylthio group or a halo-(C₁ toC₂)-alkoxy group, provided that both of R² and R³, if each representinga substituent other than a hydrogen atom, are not at the ortho positionfor the pyrimidine ring at the same time, and W¹ represents amethanesulfonyl group, or a methylthio group; provided that when W¹ is amethylthio group, R¹, R² and R³ are R¹¹, R²² and R³³, respectively,wherein R¹¹ represents a halo-(C₁ to C₆)-alkoxy group at the ortho ormeta position, R²² and R³³, which may be either the same or different,each represents a hydrogen atom, a halogen atom, a (C₁ to C₂)-alkylgroup, a halo-(C₁ to C₂)-alkyl group, a (C₁ to C₂)-alkoxy group, or ahalo-(C₁ to C₂)-alkoxy group, and both of R²² and R³³, if eachrepresenting a substituent other than a hydrogen atom, are not at theortho position for the pyrimidine ring at the same time.
 2. A compoundaccording to claim 1, wherein W¹ represents a methanesulfonyl group. 3.A compound according to claim 1, wherein W¹ represents methylthio group.